HCID 57430073, compound → HCID 59003493, compound

HRID 1169837Notes

Reaction equation

HRID 1169837 reaction equation
[C:1]([C:3]1([C:16]2[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#[N:2].[H][H]>CO.[Ni]>[NH2:2][CH2:1][C:3]1([C:16]2[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:14])([CH3:15])[CH3:13])=[O:10])[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 57430073HCID 57430073, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59003493HCID 59003493, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 4-cyano4-(3-methylpyridin-2-yl)piperidine-1-carboxylate (2 g, 6.6 mmol) in methanol (70 mL containing 2 M ammonia) was reacted with Raney nickel (1 mL of 50% slurry in water) under 45 psi hydrogen for 24 hours. The catalyst was filtered off and washed thoroughly with methanol. Evaporation of solvent afforded the desired product: tert-butyl 4-aminomethyl)4-(3-methylpyridin-2-yl)piperidine-1-carboxylate: 1H NMR δ (ppm)(CDCl3): 8.44 (1 H, br s), 7.41 (1 H, d, J=7.4 Hz), 7.07 (1 H, br s), 3.80 (2 H, br s), 3.01 (4 H, br s), 2.66 (2 H, s), 2.48 (3 H, s), 1.62-1.54 (2 H, m), 1.44 (9 H, s).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed thoroughly with methanol
  3. customEvaporation of solvent

Sources & evidence

ORD record
ord-2392b04fa9d74a64811b2f7b99c4f07f
Source dataset
uspto-grants-2010_11
Patent number
US07825135B2

Reaction notes

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