Benzaldehyde → 4-Aminomethyl-1-N-Cbz-piperidine

HRID 2304575Notes

Reaction equation

[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.C(=O)C1C=CC=CC=1.[CH2:17]([O:24][C:25](Cl)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.S([O-])(O)(=O)=O.[K+]>C1(C)C=CC=CC=1>[CH2:17]([O:24][C:25]([N:6]1[CH2:7][CH2:8][CH:3]([CH2:2][NH2:1])[CH2:4][CH2:5]1)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

22.2 g(0.2 mol) of 4-aminomethyl-piperidine was dissolved in 250 ml of toluene and then 21.2 g(0.2 mol) of benzaldehyde was added thereto. The mixture was refluxed for 3 hours with Dean-stack and cooled down to 0° C., and then 34.2 g(0.2 mol) of benzylchloroformate was added dropwise thereto while stirring. After the mixture was stirred for 3 hours, 1N aqueous potassium hydrogen sulfate solution(220 ml) was added thereto at room temperature. The mixture was extracted three times with 200 mg of diethylether, and then the aqueous layer was basified with sodium hydroxide. The aqueous solution was saturated with sodium chloride and extracted three times with 100 ml of dichloromethane. The organic solution was dried over magnesium sulfate and distilled under reduced pressure to obtain 38 g(Yield 91%, Molecular weight 248) of the title compound.

Workup

temperatureThe mixture was refluxed for 3 hours with Dean-stack
stirringAfter the mixture was stirred for 3 hours
customat room temperature
extractionThe mixture was extracted three times with 200 mg of diethylether
extractionextracted three times with 100 ml of dichloromethane
dry with materialThe organic solution was dried over magnesium sulfate
distillationdistilled under reduced pressure

Sources & evidence

ORD record: ord-c4f4bd2a53ae4661a9b5fbda6c39bc07
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06436960B1

Reaction notes

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