Tert-butyl 4-(cyanomethyl)-4-methylpiperidine-1-carboxylate → Tert-butyl 4-(2-aminoethyl)-4-methylpiperidine-1-carboxylate

HRID 1019700Notes

Reaction equation

HRID 1019700 reaction equation
[C:1]([CH2:3][C:4]1([CH3:17])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)#[N:2]>[Ni].CO>[NH2:2][CH2:1][CH2:3][C:4]1([CH3:17])[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]1

Participants

4

Reactant 1

HCID 66660780Tert-butyl 4-(cyanomethyl)-4-methylpiperidine-1-carboxylate

Product 1

HCID 66660873Tert-butyl 4-(2-aminoethyl)-4-methylpiperidine-1-carboxylateYield 94.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

The process is performed according to the procedure described in Example 12 (step 12.2.) Starting with 1.40 g (5.87 mmol) of tert-butyl 4-cyanomethyl-4-methylpiperidine-1-carboxylate (WO 2006/001 752) and 1.72 g (29.37 mmol) of Raney nickel in 20 mL of methanol under a hydrogen atmosphere (70 psi) at 45° C., 1.35 g of expected product are obtained in the form of a wax.

Workup

  1. customat 45° C.

Sources & evidence

ORD record
ord-d095e17b8f254252a9ca8c865922b042
Source dataset
uspto-grants-2014_05
Patent number
US08716289B2

Reaction notes

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