Chloroacetamide → 2-{4-[4-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-piperidin-1-yl}-acetamide

HRID 1433090Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([S:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[C:15](=[O:26])[CH2:14]3)(=[O:12])=[O:11])[S:7][C:6]=2[CH:27]=1.Cl[CH2:29][C:30]([NH2:32])=[O:31].C(N(C(C)C)CC)(C)C>CN1CCCC1=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([S:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH:20]4[CH2:21][CH2:22][N:23]([CH2:29][C:30]([NH2:32])=[O:31])[CH2:24][CH2:25]4)[C:15](=[O:26])[CH2:14]3)(=[O:12])=[O:11])[S:7][C:6]=2[CH:27]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-1-piperidin-4-ylmethyl-piperazin-2-one (20 mg, 0.047 mmol) in N-methylpyrrolidinone (0.5 mL) is added 2-chloroacetamide (9 mg, 0.094 mmole) and diisopropylethylamine (0.016 mL, 0.094 mmole) and heated at 120° C. for 16 h. The reaction is concentrated and purified by column chromatography (silica, 5% methanol/dichloromethane) to provide 2-{4-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-piperidin-1-yl}-acetamide. 1H NMR (300 MHz, CDCl3) d 7.88-7.83 (m, 3H), 7.47 (dd, 1H), 6.98 (bs, 1H), 5.30 (bs, 1H), 3.86 (s, 2H), 3.46 (s, 4H), 3.28 (d, 2H), 2.95 (s, 2H), 2.82 (d, 2H), 2.06 (t, 2H), 1.69-1.50 (m, 3H), 1.33-1.25 (m, 2H); MS (Ion spray) 485 (M+H)+.

Workup

concentrationThe reaction is concentrated
custompurified by column chromatography (silica, 5% methanol/dichloromethane)

Sources & evidence

ORD record: ord-3ffa0f9d7b334534b72caf40590f9f8d
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612075B2

Reaction notes

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