Piperidine → N-[4-Bromo-2-(2-fluorobenzoyl)phenyl]glycinamide

HRID 1365055Notes

Reaction equation

HRID 1365055 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:29])[CH2:10][NH:11]C(=O)OCC2C3C=CC=CC=3C3C2=CC=CC=3)=[C:4]([C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[F:38])=[O:31])[CH:3]=1.N1CCCCC1>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:29])[CH2:10][NH2:11])=[C:4]([C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[F:38])=[O:31])[CH:3]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 577324349H-fluoren-9-ylmethyl [2-({4-bromo-2-[(2-fluorophenyl)carbonyl]phenyl}amino)-2-oxoethyl]carbamate

Product 1

HCID 57732437N-[4-Bromo-2-(2-fluorobenzoyl)phenyl]glycinamideYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A round-bottomed flask was charged with 9H-fluoren-9-ylmethyl [2-({4-bromo-2-[(2-fluorophenyl)carbonyl]phenyl}amino)-2-oxoethyl]carbamate (580 mg) and tetrahydrofuran (15 mL). The mixture was treated with piperidine (1.5 mL) then stirred at room temperature for 1.5 h. After concentrating to an oil, the residue was taken up in methylene chloride and purified by silica gel chromatography to yield N1-{4-bromo-2-[(2-fluorophenyl)carbonyl]phenyl}glycinamide (135 mg) as a white powder. H1 NMR (d6-dmso): 8.42 (d, 1H), 7.82 (dd, 1H), 7.65-7.72 (m, 1H), 7.6 (dt, 1H), 7.52 (m, 1H), 7.33-7.40 (m, 2H), 4.0-6.4 (br s, 2H), 3.20 (s, 2H).

Workup

  1. concentrationAfter concentrating to an oil
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-9963d6298b3240139ebc40b5663f794f
Source dataset
uspto-grants-2011_02
Patent number
US07888503B2

Reaction notes

Loading…