Reaction #2358539

ord-c9b2cf240a3e405da87a91674eaf7eed

Reaction equation

CN(C)C(=O)CCCC#Cc1cccc(C(=O)NCCF)c1
3-(5-dimethylcarbamoyl-pent-1-ynyl)-N-(2-fluoro-ethyl)benzamide
→
CN(C)C(=O)CCCC=Cc1cccc(C(=O)NCCF)c1
28
Yield 40.0%
CN(C)C(=O)CCCC=Cc1cccc(C(=O)NCCF)c1
3-(5-Dimethylcarbamoyl-pent-1-enyl)-N-(2-fluoro-ethyl)-benzamide
Yield 40.0%

Reactants

CN(C)C(=O)CCCC#Cc1cccc(C(=O)NCCF)c1
3-(5-dimethylcarbamoyl-pent-1-ynyl)-N-(2-fluoro-ethyl)benzamide

Reagents

[Ni]
Ni

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Hydrogenation of 3-(5-dimethylcarbamoyl-pent-1-ynyl)-N-(2-fluoro-ethyl)benzamide (26) (0.040 g, 0.13 mmol) using BER/Ni catalyst gave 40% 28, and 55% of starting material. The mixture was separated by reverse-phase HPLC chromatography (30% acetonitrile/70% water 20 min isocratic program) to give 3-(5-dimethylcarbamoyl-pent-1-enyl)-N-(2-fluoro-ethyl)-benzamide 28 (5 mg).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09120723B2uspto-grants-2015_09