Triethylamine → HCID 68693818, compound

HRID 1169841Notes

Reaction equation

HRID 1169841 reaction equation
[C:1]([C:3]1([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[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].C(N(CC)CC)C.[H][H]>CO.[Ni]>[NH2:2][CH2:1][C:3]1([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[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

6

Reactant 3

HCID 8471TriethylamineHCID 57430079HCID 57430079, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68693818HCID 68693818, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 4-cyano-4-(6-fluoropyridin-2-yl)piperidine-1-carboxylate (250 mg, 0.82 mmol) in methanol (20 mL) with triethylamine (1 mL) was reacted with Raney nickel (0.5 mL of 50% slurry in water) under 40 psi hydrogen for 5 hours. The catalyst was filtered off and washed thoroughly with methanol. Evaporation of the solvent afforded the desired product: tert-butyl 4-(aminomethyl)-4-(6-fluoropyridin-2-yl)piperidine-1-carboxylate: m/z (ES) 310 (M+H).

Workup

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

Sources & evidence

ORD record
ord-edce26c6876840bf94eedd1499a7448d
Source dataset
uspto-grants-2010_11
Patent number
US07825135B2

Reaction notes

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