HCID 58996706, compound → HCID 67418563, compound

HRID 1803615Notes

Reaction equation

HRID 1803615 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]#[N:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>N.CCO.[Ni]>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:21][NH2:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 58996706HCID 58996706, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67418563HCID 67418563, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 22020343Ethanol, reaction products with ammonia, distn. residuesSolvent

Procedure

To a solution of 4-(2-cyano-phenyl)-perhydro-1,4-diazepine-1-carboxylic acid tert-butyl ester (905 mg, 3.0 mmol) in NH3/EtOH (2M, 15 mL) was added Raney Nickel (5 mL slurry in water). The atmosphere was exchanged with hydrogen via balloon and the mixture was allowed to stir for 2.5 h. After this time the mixture was filtered through celite and concentrated to yield the title compound (900 mg). m/z (M+1) 305.31.

Workup

  1. filtrationAfter this time the mixture was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4cd31b1d388e4786a34ea0ac3e96d168
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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