Triethylamine → HCID 57664568, compound

HRID 1467887Notes

Reaction equation

[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.C(N(CC)CC)C.[F:31][C:32]1[CH:37]=[CH:36][C:35]([CH:38]([C:43]2[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=2)[CH2:39][CH2:40][CH2:41]Cl)=[CH:34][CH:33]=1>CN(C=O)C>[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][N:21]([CH2:41][CH2:40][CH2:39][CH:38]([C:35]3[CH:34]=[CH:33][C:32]([F:31])=[CH:37][CH:36]=3)[C:43]3[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=3)[CH2:20][CH2:19]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=2)(=[O:6])=[O:7])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 85 °C

Procedure

N-Cyclopropyl-N-{1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl}-3-trifluoromethylbenzenesulfonamide (34) was prepared by dissolving N-cyclopropyl-N-piperidin-4-yl-3-trifluoromethylbenzenesulfonamide (110.6 mg, 0.318 mmol) in 10 mL of DMF and followed by the addition of triethylamine (48.3 mg, 0.477 mmol) and bis(4-fluorophenyl)butyl chloride (98.2 mg, 0.350 mmol). The reaction mixture was stirred overnight at 85° C. The crude compound was purified by column chromatography on silica gel (hexane/EtOAc, 7:3) to give the title compound 34 as a yellow sticky solid. 1H NMR (CDCl3): δ 8.12 (s, 1H), 8.04 (d, 1H), 7.84 (d, 1H), 7.61 (t, 1H), 7.13 (dd, 4H), 6.94 t, 4H), 3.84 t, 2H), 2.85 (d, 2H), 2.30 (t, 2H), 1.92 (m, 7H), 1.48 (m, 2H), 1.37 (m, 2H), 0.96 (m, 2H), 0.75 (m, 2H). LC: 100%. MS (M+H+): 593.

Workup

customN-Cyclopropyl-N-{1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl}-3-trifluoromethylbenzenesulfonamide (34) was prepared
customThe crude compound was purified by column chromatography on silica gel (hexane/EtOAc, 7:3)

Sources & evidence

ORD record: ord-4d1505ecef014b4b9277286544fb9cba
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000174B2

Reaction notes

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