Spis treści
1.
2.
23.
3.
24.
4.
5.
26.
6.
27.
7.
8.
29.
9.
30.
10.
31.
11.
32.
12.
33.
13.
34.
14.
35.
15.
36.
16.
37.
17.
38.
18.
39.
19.
40.
20.
41.
21.
42.
Spis treści
1.
2.
23.
3.
24.
4.
5.
26.
6.
27.
7.
8.
29.
9.
30.
10.
31.
11.
32.
12.
33.
13.
34.
14.
35.
15.
36.
16.
37.
17.
38.
18.
39.
19.
40.
20.
41.
21.
42.
OH
OH
O
O
OH
O
O
AlCl
3
OOH
H
2
SO
4
OH
NaOH
ONa
CO
2
O
ONa
O
OH
O
ONa
[H
3
O+]
(CH
3
CO)
2
O
[O]
Cu, kat., 120*C
90-120*C, p
175*C
p
benznen
Aspiryna
NO
2
H
2
SO
4
HNO
3
NO
2
NO
2
(NH
4
)
2
S
NO
2
N
N
SO
3
H
NO
2
NH
2
NaNO
2
H
2
SO
4
OH
2
Cu
NO
2
OH
Fe/HCl
H
2
O, T
NH
2
OH
K
2
CO
3
, CO
2
T
NH
2
OH
HOOC
Kwas p-aminosalicylowy
Imipramina
Cl
NO
2
KOH
ETOH
NO
2
O
2
N
Cl
n
NO
2
O
2
N
SnCl
2
ClH
NH
2
N
H
2
BuOH, Na
NH
2
N
H
2
NH
4
Cl
N
H
benzen
Cl
N
NaNH
2
N
N
o-o-dinirtostyren
270*C
Chlorpromazyna
N
H
2
Cl
Cl
COOH
K
2
CO
3
T
N
Cl
COOH
H
DEL
-CO
2
N
Cl
H
S, I
2
DEL
N
Cl
H
S
Cl
N
NaNH
2
N
Cl
S
N
+
Tropikamid
COOEt
EtONa
HCOOEt
COOEt
NaO
H
H
3
O+
COOEt
O
NaBH
4
COOEt
OH
NaOH
OH
COOH
1
. Ac
2
O
2
. SOCl
2
OAc
COCl
N
N
H
Et
1
. pirydyna
2
. HCl
3
. NH
3
H
2
O
O
H
O
N
Et
N
Escilopram
O
O
CN
MgBr
F
O
O
CN
F
MgBr
CN
O
OMgBr
F
N
MgBr
CN
OMgBr
F
OMgBr
N
AcOH
CN
OH
F
OH
N
MeSOCl
2
TEA
CN
F
N
O
+
rozdzielanie kwasem p-toluenowinowym
hydroliza t-BuOK
S
Stilbestrol
O
O
O
O
OH
O
O
O
O
SnCl
2
, HCl
O
O
O
O
O
OH
CH
3
COCl
-H
2
O
O
O
O
H
OH
KCN
EtI
EtONa
EtMgBr
KOH
220*C
Oksazepam
Cl
NH
2
Cl
O
ZnCl
2
Cl
NH
O
O
i
Cl
NH
2
O
AcOH
H
2
SO
4
NH
2
OH
Cl
NH
2
N
OH
AcOH
ClCH
2
COCl
Cl
N
N
O
Cl
NaOH
N
N
O
O
Cl
AcOH
N
N
O
Cl
OAc CH
3
NH
2
N
N
O
Cl
OH
Buspiron
N
N
N
N
Cl
N
N
N
N
N
+
N
N
N
Br
Br
Br
K
2
CO
3
, benzen
N
O
O
N
O
O
N
N
N
N
K
2
CO
3
toluen
eter koron.
+
nadmiar
Tramadol
NO
2
Br
2
, AlCl
3
NO
2
Br
Fe, HCl
NH
2
Br
1
. NaNO
2
, HCl
2
. CuCl
2
, H
2
O, T
OH
Br
(CH
3
)
2
SO
4
/OH-
O
Br
O
MgBr
O
N
*
*
O
N
O
H
1
.
2
. NH
4
Cl
180*C
Mg/THF
Fentanyl
NH
2
O
O
N
O
O
O
O
MeOH
N
O
O
O
1
. H
2
O, OH-
2
. -CO
2
N
O
NH
2
N
N
N
N
O
O
1
. [H]
2
. ClCOOEt
+
kondensacja
Dickmanna
ksylen
Pentazocyna
N
CH
3
I
N
+
O
MgCl
N
O
H
2
/Pd
N
O
T
O
H
N
O
H
N
Br
O
H
N
K
2
CO
3
BrCN
Lidokaina
NH
2
Cl
O
Cl
N
O
Cl
N
O
N
N
T
+
Bupiwakaina
NH
2
N
O
Cl
N
O
N
Br
N
O
N
+
Br
H
2
, PtO
N
O
N
+
Ropiwakaina
N
OH
O
PCl
5
N
Cl
O
N
H
2
N
N
O
Br
N
N
O
1
. K
2
CO
3
2
. HCl
Karbamazepina
N
O
Cl
Cl
N
O
Cl
NH
3
EtOH
N
O
NH
2
Mefenytoina
CN
O
O
O
O
O
CN
NH
3
O
NH
2
CN
Br
O
NH
2
CN
N
N
O
O
(CH
3
)
2
SO
4
N
N
O
O
+
NaOH
Haloperidol
NH
2
O
O
N
O
O
O
O
Na
ksylen
N
ONa
O
OH
HCl aq
DEL
N
O
Cl
MgBr
N
OH
Cl
Pd/C, H
2
MeOH
N
OH
Cl
O
Cl
F
N
OH
Cl
O
F
+
MeOH
Olanzapina
C
2
H
5
CHO
S
CH
2
(CN)
2
Et
3
N
S
N
H
2
NC
SnCl
2
F
NO
2
N
S
NO
2
CN
N
N
S
NH
2
N
N
N
N
S
N
N
+ +
HCl
NaH
*HCl
DMSO
Indometacyna
OH
NO
2
(CH
3
)
2
SO
4
OH-
O
NO
2
Fe, HCl
O
NH
2
NaNO
2
ClH
O
N
+
N
Cl
Na
2
SO
4
Zn
O
NHNH
2
H
2
CO
O
NHNH
2
Cl
O
Cl
O
NHNH
2
O
Cl
O
NHNH
2
O
Cl
COOH
N
O
O
OH
O
Cl
*CHO
*CHO
Diltiazem
O
O
Cl
O
O
CH
3
ONa
O
O
O
O
SH
NO
2
O
S
O
O
OH
NO
2
1
. NaOH
2
. L-lizyna
O
S
O
O
OH
NO
2
1
. Pd, H
2
2
. DEL, ksylen
S
N
OH
O
O
Ac
2
O
S
N
O
O
O
O
Cl
N
S
N
O
O
O
O
N
Tolbutamid
ClSO
2
OH
SO
2
Cl
SO
2
Cl
(NH
4
)
2
CO
3
SO
2
NH
2
ClCOOEt
SO
2
N
H
COOEt
n-BuNH
2
SO
2
N
H
O
N
T
nadmiar
40*C
+
rozdzial
T, f. stala
Ibuprofen
CH
3
COCl
AlCl
3
O
ClCH
2
COOEt
EtONa
O
O
O
H
3
O+
O
NH
2
OH
N
OH
-H
2
O
N
H
3
O+
O
OH
O
O
O
H
OH
H
H
EtOOC
COOEt
H
3
O+, -H
2
O
p-TSA lub HCl g
O
O
O
H
H
EtOOC
COOEt
Br
2
, hv
O
O
O
H
H
EtOOC
COOEt
H
Br
Br
1
. NaOH aq
2
. AgBF
4
O
Br
O
O
OH
H
H
H
HOOC
COOH
1
. H
3
O+
2
. Pd/C, HCOONH
2
O
H
COOH
+
(R,R,S) 99%
Naproksen
Timolol
S
N
N
Cl
Cl
N
O
S
N
N
N
Cl
O
NaOH
S
N
N
N
O
H
O
S
N
N
N
O
O
O
O
Cl
NaOH
NH
2
S
N
N
N
O
O
OH
N
S
N
N
N
O
O
OH
N
H
+
(+)kw. winowy
S
Kaptopryl
COOH
SH
O
COOH
S
O
SOCl
2
S
O
COCl
N
COOH
O
O
Cl
N
COOH
O
O
NaOH
H
2
SO
4
N
O
O
O
O
Pd, H
2
N
O
O
S
O
COCl
NaOH
N
O
O
O
S
O
1
. CF
3
COOH
N
OH
O
O
S
H
2
. NH
3
, MeOH
+
+
po 1. rozdzial
S, S
L-Dopa
AcO
NHAc
OMe
COOH
kat. chiralny
H2
AcO
NHAc
OMe
COOH
H
O
H
NH
2
O
H
COOH
H
Testosteron cz.1
O
H
H
H
Ac
2
O
AcO
H
H
Br
2
AcO
H
H
Br
Br
CrO
3
CH
3
COOH
AcO
H
H
Br
Br
O
1
. Zn
2
. NH
2
NHCONH
2
NH
2
NHCONH
2
AcO
H
H
1
. H
2
SO
4
2
. KOH, N
2
O
O
H
H
H
Testosteron cz.2
O
O
H
H
H
O
AcO
H
H
Ac
2
O
na zimno
H
2
, lagodne
OH
AcO
H
H
H
BnCOCl
OCOBn
AcO
H
H
H
KOH
OCOBn
O
H
H
H
H
OCOBn
O
H
H
H
KOH
OH
O
H
H
H
O
(EtCO)
2
O
OCOEt
O
H
H
H
[O]
Progesteron
O
AcO
H
H
HCN
OH
O
H
H
H
NC
POCl
3
N
O
H
H
H
CN
CH
3
MgBr
AcOH
O
H
H
H
O
Ni, H
2
O
H
H
H
O
O
H
H
O
Estradiol
OCOBn
O
H
H
H
H2
OCOBn
O
H
H
H
H
H
CrO
3
OCOBn
O
H
H
Br
2
OCOBn
O
H
H
Br
Br
kolid.
-HBr
OCOBn
O
H
H
KOH
OH
O
H
H
tetralina
OH
O
H
H
H
-CO
2
600*C
Chloramfenikol
NO
2
KMnO
4
O
NO
2
Br
2
O
NO
2
Br
O
NO
2
(CH
2
)
6
N
4
Br
HCl, EtOH
O
NO
2
NH
3
Cl
AcOH
AcONa
O
NO
2
N
H
Ac
HCOH
NaHCO
3
*
O
NO
2
N
H
Ac
OH
(i-Pr)
3
Al
*
*
O
H
NO
2
N
H
Ac
OH
ClH
*
*
O
H
NO
2
NH
2
OH
2
. Cl
2
CHCOOEt
*
*
O
H
NO
2
N
H
OH
O
Cl
Cl
lekko zas.
chlodzenie
urotropina
racemat
racemat
1. kw. winowy
Salbutamol
OAc
COOH
CH
3
COCl
AlCl
3
OAc
COOH
O
ClH
MeOH
OH
O
COOMe
Br
2
CHCl
3
OH
O
COOMe
Br
LiAlH
4
THF
N
OH
O
COOMe
N
OH
O
H
N
OH
H
2
, Pd/C
OH
O
H
N
OH
(-) 68 x silniejszy od (+)
Zafirlukast
O
OH
O
MeOH
SOCl
2
O
O
O
Br
2
O
O
O
Br
N
O
2
N
N
O
2
N
O
O
O
N
N
H
2
O
O
O
O
Cl
O
N
N
H
O
O
O
O
O
1
. LiOH H
2
O
2
.
S
O
O
N
H
N
N
H
O
O
O
O
2
.
S
O
O
N
H
2
uv
Cu
2
O
EtOAc
RaNi, H
2
EtOAc
MeOH
DCC, DMAP
1,4-dioksan
Ketokonazol
O
Br
Cl
Cl
OH
OH
O
H
O
O
Br
Cl
Cl
O
H
p-TSA
1
.
2
.
Cl
O
N
N
N
N
O
O
Cl
Cl
O
O
N
N
O
O
Cl
Cl
O
S
O
O
1
. NaOH
2
. MeSO
2
Cl
N
N
O
OH
NaH
N
N
O
O
Cl
Cl
O
N
N
O
nasadka D-S
+
Binazyna
O
O
O
Zn, AcOH
ClH
O
O
Br
2
, hv
O
O
Br
OH
O
O
NH
2
NH
2
N
O
N
N
N
OH
NaCl
N
N
Cl
NH
2
NH
2
H
2
O
N
N
N
NH
2
Cl
O
O
N
N
N
H
N
H
O
O
Zolpidem
N
NH
2
O
Br
N
N
N
O
N
N
N
CH
3
I
NaCN
N
N
NC
O
O
O
O
1
. HCl
2
. POCl
3
3
.
N
N
N
N
O
+
Furosemid
Cl
Cl
SO
2
Cl
Cl
Cl
SO
2
NH
2
Cl
Cl
SO
2
NH
2
Cl
Cl
COOH
SO
2
NH
2
Cl
N
H
COOH
O
N
H
2
O
HSO
3
Cl
NH
3
KMnO
4
Hydrochlorotiazyd
NH
3
Cl
Cl
HSO
3
Cl
NH
2
Cl
SO
2
SO
2
Cl
Cl
NH
3
NH
2
Cl
SO
2
SO
2
N
H
2
NH
2
HCOH
Cl
SO
2
N
H
2
NH
N
H
S
O
O
NaOH
Cl
SO
2
NaHN
NH
N
S
O
O
HCOOH
Cl
SO
2
N
H
2
NH
N
S
O
O
Klemastyna
Cl
O
MgBr
1
.
2
. NH
4
Cl
Cl
OH
N
Cl
NaH, ksylen
N
O
Cl
N
O
Cl
1. kryst. z malinianu
2. redukcja z (-)dibenzoilo
-L-winowym kwasem
Loratydyna
N
NC
O
H
st. H
2
SO
4
N
N
O
1
. BuLi, heksan, THF, NaBr
Cl
Cl
2
. THF,
N
N
O
Cl
POCl
3
reflux
N
Cl
NC
N
MgCl
N
Cl
O
N
BF
3
, HF,
-H
3
O+
N
N
Cl
IH
Cl
O
O
N
N
Cl
O
O
+
1. 70*C
2. 75*C
-40*C
-35*C
toluen, 80*C
Naratriptan
N
Br
N
O
N
Br
N
O
H
S
N
O
O
N
N
S
N
O
O
H
2
, Pd/C, DMF, H
2
O
N
N
S
N
O
O
KOH, MeOH, 20*C
DMF, 110*C
Chlodiazepoksyd
Cl
NH
2
Cl
O
ZnCl
2
Cl
NH
O
O
i
Cl
NH
2
O
AcOH
H
2
SO
4
NH
2
OH
Cl
NH
2
N
OH
AcOH
ClCH
2
COCl
Cl
N
N
O
Cl
N
N
O
Cl
N
CH
3
NH
2
Prezentacja wykonana na podstawie notatek Kasi Rybickiej,
google.com i własnej wiedzy.
Proszę korzystać do woli, ale nie rozprzestrzeniać.
Uwagi,
Przemo Taciak.