Benzyl chloroformate → HCID 67366402, compound
Reaction equation
[C:1](Cl)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C([N:19]1[CH2:24][CH2:23][C:22]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([N:25]([CH3:27])[CH3:26])[CH2:21][CH2:20]1)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>CO.C(Cl)(Cl)Cl>[CH2:4]([O:3][C:1]([N:19]1[CH2:24][CH2:23][C:22]([N:25]([CH3:27])[CH3:26])([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:21][CH2:20]1)=[O:2])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
500 ml (10 equiv.) of Cbz chloride were added dropwise, over a period of 1 hour, to 50 g (1 equiv.) of 1-benzyl-N,N-dimethyl-4-phenylpiperidine-4-amine, and the resulting reaction mixture was stirred for 2 hours at room temperature. The progress of the reaction was monitored by thin-layer chromatography (10% MeOH/CHCl3). When the reaction was complete, the mixture was cooled to 0° C. and rendered basic with saturated sodium hydrogen carbonate solution, and the reaction mixture was extracted 3× with 300 ml of EtOAc. The combined organic phases were dried with Na2SO4. After removal of the solvent under reduced pressure, purification was carried out by column chromatography (silica gel; 50% EtOAc/heptane). 12 g (21%) of product were obtained in the form of an oil.
Workup
- customthe resulting reaction mixture
- temperaturethe mixture was cooled to 0° C.
- extractionthe reaction mixture was extracted 3× with 300 ml of EtOAc
- dry with materialThe combined organic phases were dried with Na2SO4
- customAfter removal of the solvent
- customunder reduced pressure, purification
Sources & evidence
- ORD record
- ord-67d0c36e8bd345ce81afdae822e1aa93
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08269000B2
Reaction notes
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