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
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
500 ml (10 eq.) Cbz chloride were added dropwise to 50 g (1 eq.) 1-benzyl-N,N-dimethyl-4-phenylpiperidin-4-amine over a period of 1 h and the reaction mixture obtained was stirred for 2 h at room temperature. The reaction course was monitored by thin-layer chromatography (10% MeOH/CHCl3). Once the conversion was complete, the reaction mixture was cooled to 0° C., made alkaline with saturated sodium hydrogen carbonate solution and extracted 3 times with 300 ml EtOAc. The combined organic phases were dried with Na2SO4. Following removal of the solvent under reduced pressure, the residue was purified by column chromatography (silica gel; 50% EtOAc/heptane). 12 g (21%) of product were obtained in the form of an oil.
Workup
- customthe reaction mixture obtained
- temperaturethe reaction mixture was cooled to 0° C.
- extractionextracted 3 times with 300 ml EtOAc
- dry with materialThe combined organic phases were dried with Na2SO4
- customremoval of the solvent under reduced pressure
- customthe residue was purified by column chromatography (silica gel; 50% EtOAc/heptane)
Sources & evidence
- ORD record
- ord-d1540ac7271e48589aa9094a04993786
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492559B2
Reaction notes
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