Tert-butyl 4-(3-bromobenzylidene)piperidine-1-carboxylate → Tert-butyl 4-(3-bromobenzyl)piperidine-1-carboxylate

HRID 657371

Reaction equation

HRID 657371 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 57813409Tert-butyl 4-(3-bromobenzylidene)piperidine-1-carboxylate

Product 1

HCID 57813365Tert-butyl 4-(3-bromobenzyl)piperidine-1-carboxylateYield 94.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,1-dimethylethyl 4-[(3-bromophenyl)methylidene]-1-piperidine-carboxylate (201 mg, 0.571 mmol) in THF (1 mL) was applied onto an H-Cube hydrogenation device (H-Cube, LLC, Dallas, Tex., USA; http://www.h-cubeinc.com/) 10% PD/C at a flow rate of 1 mL/min and 1 atm H2. The mixture was concentrated to afford the title compound 0.1909 g (94%). LC-MS m/z 354 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-b62258759272445bb08eaa7978bd59e3
Source dataset
uspto-grants-2011_12
Patent number
US08071588B2

Linked notes

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