Tert-butyl 3-cyano-3-(1-methylpiperidin-2-yl)azetidine-1-carboxylate → Tert-butyl 3-(aminomethyl)-3-(1-methylpiperidin-2-yl)azetidine-1-carboxylate

HRID 2100311Notes

Reaction equation

HRID 2100311 reaction equation
[C:1]([C:3]1([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][N:15]2[CH3:20])[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4]1)#[N:2]>N.CO.[Ni]>[NH2:2][CH2:1][C:3]1([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][N:15]2[CH3:20])[CH2:4][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6]1

Participants

5

Reactant 1

HCID 57798312Tert-butyl 3-cyano-3-(1-methylpiperidin-2-yl)azetidine-1-carboxylate

Product 1

HCID 57798322Tert-butyl 3-(aminomethyl)-3-(1-methylpiperidin-2-yl)azetidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

tert-Butyl 3-cyano-3-(1-methylpiperidin-2-yl)azetidine-1-carboxylate (8.1 g, 29 mmol) was dissolved in 2M ammonia in methanol (100 ml) and Raney nickel (50% slurry in water, 5.0 g (2.5 g Raney nickel)) was added and the mixture hydrogenated on a parr at 45 psi for 1 day until tlc showed completion. The reaction was filtered under nitrogen and the filtrate was evaporated to dryness to give tert-Butyl 3-(aminomethyl)-3-(1-methylpiperidin-2-yl)azetidine-1-carboxylate as an oil. m/z (M++H) 284.

Workup

  1. filtrationThe reaction was filtered under nitrogen
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-7f15cc53d30c4af2801579472df3ad64
Source dataset
uspto-grants-2009_08
Patent number
US07572792B2

Reaction notes

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