HCID 66660889, compound → 1,1-Dimethylethyl 4-(2-aminoethyl)-4-ethyl-1-piperidinecarboxylate

HRID 1019703Notes

Reaction equation

HRID 1019703 reaction equation
[C:1]([CH2:3][C:4]1([CH2:17][CH3:18])[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([CH2:17][CH3:18])[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH2:8][CH2:9]1

Participants

4

Reactant 1

HCID 66660889HCID 66660889, compound

Product 1

HCID 666610681,1-Dimethylethyl 4-(2-aminoethyl)-4-ethyl-1-piperidinecarboxylateYield 72.3%

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 0.96 g (3.83 mmol) of tert-butyl 4-cyanomethyl-4-ethylpiperidine-1-carboxylate and 1.12 g (19.15 mmol) of Raney nickel in 50 mL of methanol under a hydrogen atmosphere (70 psi) at 50° C., and after chromatography on a column of silica gel, eluting with a 95/5/0.5 mixture of dichloromethane, methanol and 28% aqueous ammonia, 0.71 g of expected product is obtained in the form of a wax.

Workup

  1. customat 50° C.
  2. washafter chromatography on a column of silica gel, eluting with a 95/5/0.5 mixture of dichloromethane, methanol and 28% aqueous ammonia

Sources & evidence

ORD record
ord-98a10a57e3ad4583b5c1eff4e44b8906
Source dataset
uspto-grants-2014_05
Patent number
US08716289B2

Reaction notes

Loading…