Triethylamine → HCID 178501233, compound

Reaction equation

Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:5][CH2:4]1.[Cl:13][CH2:14][CH2:15][CH2:16][C:17](Cl)=[O:18].C(N(CC)CC)C>ClCCl>[Cl:13][CH2:14][CH2:15][CH2:16][C:17]([NH:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:8]1)=[O:18]

Participants

Procedure

Methyl trans-4-aminocyclohexanecarboxylate hydrochloride (45.31 g) is suspended in dichloromethane (1000 ml), thereto is added 4-chlorobutyryl chloride (31.5 ml) under ice-cooling and to the mixture is added dropwise a solution of triethylamine (81.5 ml) in dichloromethane (80 ml). The reaction solution is warmed to room temperature, stirred for 3 hours and the reaction solution is concentrated under reduced pressure. To the resulting residue are poured ethyl acetate and 5% hydrochloric acid, and the organic layer is separated, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer is dried over sodium sulfate and treated with activated carbon, and the filtrate is concentrated under reduced pressure. The resulting residue is suspended in diisopropyl ether, filtered to collect the precipitates, dried to give methyl trans-4-(4-chlorobutyrylamino)cyclohexanecarboxylate (38.81 g).