HCID 66818527, compound → HCID 66818689, compound

HRID 1024771Notes

Reaction equation

HRID 1024771 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:29])[C:13]2[CH:18]=[C:17]([OH:19])[CH:16]=[C:15]([O:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=3)[CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]>[Ni].N>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:29])[C:13]2[CH:18]=[C:17]([OH:19])[CH:16]=[C:15]([O:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][NH2:28])=[CH:23][CH:22]=3)[CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 66818527HCID 66818527, compound

Product 1

HCID 66818689HCID 66818689, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

Raney nickel (0.1 g, 1.7 mmols) was added to a stirred solution of 4-[3-(4-cyano phenoxy)-5-hydroxy benzoyl]piperazine-1-carboxylic acid ethyl ester (0.5 g, 1.26 mmols) dissolved in methanolic ammonia (50 ml) and the reaction mixture was heated to 50° C. in Paar apparatus under 50 Psi hydrogen gas pressure for 3 h. The reaction mixture was cooled and filtered through celite pad. The filtrate was concentrated to afford 0.4 g of the required product which was used for the next step without further purification. Percentage purity (LCMS): 74.3%, (M+1)=399.1+1.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered through celite pad
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5ba1d5c895c747689928901e12408f85
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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