Ammonia → 4-(3-Aminopropyl)-4-cyclohexylpiperidine-1-carboxylic acid tert-butyl ester

HRID 1795175Notes

Reaction equation

HRID 1795175 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH:20]=[CH:21][C:22]#[N:23])([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N>CO.[Ni]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:20][CH2:21][CH2:22][NH2:23])([CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 695970864-(2-Cyanovinyl)-4-cyclohexylpiperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 210237744-(3-Aminopropyl)-4-cyclohexylpiperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(2-cyanovinyl)-4-cyclohexylpiperidine-1-carboxylic acid tert-butyl ester, 14, (800 mg, 2.35 mmol) in MeOH (33 mL) is added ammonia (16 mL) and Raney Ni (50 mg). The reaction mixture is degassed with nitrogen, purged with hydrogen gas and shaken under an atmosphere of hydrogen (45 psi) on a standard hydrogenation apparatus at room temperature for 6 hours. The reaction solution is filtered to remove the catalyst and the solvent removed in vacuo to afford the desired product was obtained as a colorless, sticky oil in quantitative yield.

Workup

  1. customThe reaction mixture is degassed with nitrogen
  2. custompurged with hydrogen gas
  3. filtrationThe reaction solution is filtered
  4. customto remove the catalyst
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-6d37f3a415b64af89315f71cd3701724
Source dataset
uspto-grants-2006_04
Patent number
US07026335B2

Reaction notes

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