Pyridine → (4-Dimethylamino-4-phenylcyclohexylmethyl)-carbamic acid 4-nitrophenyl ester
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11](Cl)=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][C:19]([N:28]([CH3:30])[CH3:29])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18][CH2:17]1.N1C=CC=CC=1>C(Cl)Cl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11](=[O:12])[NH:14][CH2:15][CH:16]2[CH2:17][CH2:18][C:19]([N:28]([CH3:30])[CH3:29])([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:20][CH2:21]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]Participants
5
Procedure
The chloroformic acid 4-nitrophenyl ester (913.5 mg, 4.53 mmole) dissolved in abs. DCM (15 ml) was slowly added dropwise while cooling in ice water to a solution of (4-aminomethyl-1-phenylcyclohexyl)-dimethylamine (1 g, 4.3 mmole) in abs. DCM (15 ml) and pyridine (766 μl, 9.49 mmole). The reaction mixture was then stirred for 20 hours at RT. The red reaction mixture was worked up by washing with water (3×10 ml), with 1M HCl (3×10 ml) and with 1M NaOH (2×10 ml). The organic phase was dried with Na2SO4 and then concentrated by evaporation. The residue was a mixture of the diastereoisomers of (4-dimethylamino-4-phenylcyclohexylmethyl)-carbamic acid 4-nitrophenyl ester (1.25 g, reddish-brown oil, 73%).
Workup
- customThe red reaction mixture
- washby washing with water (3×10 ml), with 1M HCl (3×10 ml) and with 1M NaOH (2×10 ml)
- dry with materialThe organic phase was dried with Na2SO4
- concentrationconcentrated by evaporation
- additiona mixture of the diastereoisomers of (4-dimethylamino-4-phenylcyclohexylmethyl)-carbamic acid 4-nitrophenyl ester (1.25 g, reddish-brown oil, 73%)
Sources & evidence
- ORD record
- ord-ffca087ce9774dfa873f520cfc41d6eb
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07759385B2
Reaction notes
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