HCID 66878228, compound → HCID 66877986, compound

HRID 1878324Notes

Reaction equation

HRID 1878324 reaction equation
[C:1]([NH:5][C:6](=[O:31])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][N:14]2[CH2:19][CH2:18][N:17]([C:20](=[O:30])[C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=3)[CH2:16][CH2:15]2)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Ni]>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([C:20]([N:17]2[CH2:18][CH2:19][N:14]([CH2:13][C:9]3[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=3)[C:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:31])[CH2:15][CH2:16]2)=[O:30])=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 66878228HCID 66878228, compoundHCID 178418361HCID 178418361, compound3×

Product 1

HCID 66877986HCID 66877986, compoundYield 67.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

N-tert-Butyl-3((4-(4-nitrobenzoyl)piperazin-1-yl)methyl)benzamide (0.56 g, 1.31 mmol) was dissolved In methanol (10 mL) at room temperature. Raney 2800 nickel (−1mL of an aqueous suspension) was added and the grey suspension was stirred vigorously. A balloon of hydrogen was attached to the flask via a three-way stopcock and hydrogen was allowed to slowly flow through the system for 1 minute. The flask was sealed under 1 atmosphere of hydrogen and vigorous stirring continued for 1 hour. The balloon was removed and the flask was flushed with argon. The suspension was gravity-filtered over fluted paper and washed with methanol. The filtrate was concentrated to a crude foam/glass and silica chromatography (70-90% ethyl acetate in n-hexanes with 1-3% methanol, followed by 1-6% methanol in dichloromethane) gave the title compound (0.35 g).

Workup

  1. stirringvigorous stirring
  2. waitcontinued for 1 hour
  3. customThe balloon was removed
  4. customthe flask was flushed with argon
  5. filtrationThe suspension was gravity-filtered
  6. washwashed with methanol
  7. concentrationThe filtrate was concentrated to a crude foam/glass and silica chromatography (70-90% ethyl acetate in n-hexanes with 1-3% methanol, followed by 1-6% methanol in dichloromethane)

Sources & evidence

ORD record
ord-48c21cc7d2264242b1ddc6fee441b1b5
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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