2,2-Diphenylacetyl chloride → N-[3-(1-{2-[(Diphenylacetyl)amino]ethyl}-4-piperidinyl)phenyl]-2-methylpropanamide

HRID 1832235Notes

Reaction equation

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

Participants

Conditions

Temperature: 23 °C

Procedure

A mixture of N-{3[1-(2-aminoethyl)-4-piperidinyl]phenyl}-2-methylpropanamide (20.0 mg, 0.0700 mmol), diphenylacetyl chloride (23.0 mg, 0.110 mmol), and TEA (20.0 mg, 0.140 mmol) in THF (2 mL) was stirred overnight at 23° C. The crude product was purified by preparative TLC using CH2Cl2/MeOH/isopropyl amine (19:1:0.2) to give the desired product (8.0 mg, 47%). 1H NMR (400 MHz, CDCl3) δ 7.53 (s, 1H) 7.37–7.20 (m, 13H), 6.97–6.92 (m, 1H) 6.67 (s, 1H) 4.98 (s, 1H), 3.43 (q, 2H, J=5.9 Hz), 2.90 (d, 2H, J=11.6 Hz), 2.57–2.42 (m, 4H), 2.11 (t, 2H, J=10.4 Hz), 1.75 (d, 2H, J=12.4 Hz), 1.70–1.58 (m, 2H), 1.25 (d, 6H, J=6.7 Hz); ESMS m/e: 484.2 (M+H)+.

Workup

customThe crude product was purified by preparative TLC

Sources & evidence

ORD record: ord-32d085f6e9064b7f98b9fed492550756
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067534B1

Reaction notes

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