tert-Butyl 4-(cyanoacetyl)piperazine-1-carboxylate → HCID 28505605, compound

HRID 1726022Notes

Reaction equation

HRID 1726022 reaction equation
[C:1]([CH2:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[O:5])#[N:2]>[OH-].[NH4+].CO.[Ni]>[NH2:2][CH2:1][CH2:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[O:5]

Participants

5

Reactant 1

HCID 18946315tert-Butyl 4-(cyanoacetyl)piperazine-1-carboxylate

Product 1

HCID 28505605HCID 28505605, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 14923Ammonium HydroxideSolvent

Procedure

A mixture of Example 604A (500 mg) was hydrogenated in the presence of Raney® nickel (5 g) in 10 mL of 20% ammonium hydroxide in methanol at room temperature for 16 hours under 60 psi pressure. Insoluble was filtered off and the filtrate was evaporated to dryness and the residue was redissolved in ether. The ethereal solution was passed through membrane filter. The title compound was obtained after ether was removed. 330 mg. MS (ESI(+)) m/e 258 (M+H)−; 1H NMR (300 MHz, DMSO-d6) δ 4.04 (s, 2H), 3.42-3.45 (m, 4H), 3.26-3.33 (m, 42H), 1.41 (s, 9H).

Workup

  1. filtrationInsoluble was filtered off
  2. customthe filtrate was evaporated to dryness
  3. dissolutionthe residue was redissolved in ether
  4. filtrationfilter

Sources & evidence

ORD record
ord-a07a99eb52dc4c6094bf374c2f5a94db
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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