Reaktion #53924

Reaktionsgleichung

trans-Methanesulfonic acid 4-{4-[(4-chloro-phenoxycarbonyl)-methyl-amino]-cyclohexyl}-but-3-ynyl ester

Dimethylamine

→

trans-[4-(4-Dimethylamino-but-1-ynyl)-cyclohexyl]-methyl-carbamic acid 4-chloro-phenyl ester

Ausbeute 34.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was heated at 70° C. for 2 h
2. 2
   Temperaturcooled
3. 3
   Sonstigeevaporated
4. 4
   Extraktionthe residue extracted with aqueous saturated NaHCO3/Et2O (3×)
5. 5
   TrocknenThe organic phase was dried with Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated
8. 8
   SonstigePurification by flash column chromatography on silica gel (CH2Cl2/MeOH 99:1 to 9:1)

Vorschrift

A solution of 400 mg (corresponds to 0.69 mmol) of crude trans-Methanesulfonic acid 4-{4-[(4-chloro-phenoxycarbonyl)-methyl-amino]-cyclohexyl}-but-3-ynyl ester in 4 ml of methanol was treated with 1.23 ml (6.88 mmol) Dimethylamine (33% in EtOH, 5.6M) and stirred over night at RT. The reaction was heated at 70° C. for 2 h, cooled, evaporated and the residue extracted with aqueous saturated NaHCO3/Et2O (3×). The organic phase was dried with Na2SO4, filtered and evaporated. Purification by flash column chromatography on silica gel (CH2Cl2/MeOH 99:1 to 9:1) gave 84 mg (34%) of trans-[4-(4-Dimethylamino-but-1-ynyl)-cyclohexyl]-methyl-carbamic acid 4-chloro-phenyl ester, MS: 363 (MH+, 1Cl).

Quelle