4-Fluorophenylacetyl chloride → N-{3-[1-((3S)-3-{[(4-Fluorophenyl)acetyl]amino}-3-phenylpropyl)-4-piperidinyl]phenyl}-2-methylpropanamide

HRID 1832213Notes

Reaction equation

HRID 1832213 reaction equation
[NH2:1][C@H:2]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:22])[CH:19]([CH3:21])[CH3:20])[CH:14]=[CH:15][CH:16]=2)[CH2:7][CH2:6]1.[F:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37](Cl)=[O:38])=[CH:32][CH:31]=1>C1COCC1>[F:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37]([NH:1][C@H:2]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:3][CH2:4][N:5]2[CH2:10][CH2:9][CH:8]([C:11]3[CH:12]=[C:13]([NH:17][C:18](=[O:22])[CH:19]([CH3:21])[CH3:20])[CH:14]=[CH:15][CH:16]=3)[CH2:7][CH2:6]2)=[O:38])=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 37449884-Fluorophenylacetyl chlorideHCID 69523474N-(3-(1-[(3S)-3-amino-3-phenylpropyl]-4-piperidinyl)phenyl)-2-methylpropanamide

Product 1

HCID 60078719N-{3-[1-((3S)-3-{[(4-Fluorophenyl)acetyl]amino}-3-phenylpropyl)-4-piperidinyl]phenyl}-2-methylpropanamideYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-(3-{1-[(3S)-3-amino-3-phenylpropyl]-4-piperidinyl}phenyl)-2-methylpropanamide (11.0 mg, 0.0280 mmol) and (4-fluorophenyl)acetyl chloride (7.20 mg, 0.0420 mmol) in THF (5 mL) was stirred at room temperature for 4 h. The solvent was removed under reduced pressure and the residue was purified by preparative TLC using Hexane:EtOAc (2:1) to give the desired product (13 mg, 90% yield). 1H NMR (400 MHz, CDCl3) δ 7.89 (d, 1H, J=8.4 Hz), 7.59 (s, 1H), 7.31–6.93 (m, 13H), 5.13 (q, 1H, J=6.0 Hz), 3.56 (s, 2H), 3.07 (d, 1H, J=11.7 Hz), 2.91 (d, 1H, J=11.0 Hz), 2.62–2.42 (m, 2H), 2.40–2.30 (m, 1H), 2.12–1.54 (m, 9H), 1.24 (d, 6H, J=6.7 Hz); ESMS m/e: 515.3 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-aa85a59b46884516bbb7116ff00bbf5a
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

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