Triethylamine → HCID 57664592, compound

HRID 1467867Notes

Reaction equation

[CH:1]1([N:4]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:31][CH:30]=1>CN(C=O)C>[CH:1]1([N:4]([CH:14]2[CH2:19][CH2:18][N:17]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)=[CH:31][CH:30]=3)[CH2:16][CH2:15]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)(=[O:6])=[O:7])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

N-Cyclopropyl-N-piperidin-4-yl-benzenesulfonamide (56 mg, 0.2 mmol) was dissolved in DMF (2.5 ml) and triethylamine (75 μL, 54 mg, 0.54 mmol) added, followed by 4-chloromethyl-biphenyl (81 mg, 0.4 mmol). The reaction mixture was stirred for 12 hours at 80° C. and the solvent was evaporated. The residue was purified by flash chromatography to give 16.4 mg of the desired product N-cyclopropyl-N-[1-(4-phenylbenzyl)piperidin-4-yl]benzenesulfonamide (16). 1H NMR (CDCl3): δ 7.92-7.85 (m, 1H), 7.63-7.31 (m, 9H), 7.30-7.25 (m, 4H), 3.93-3.83 (m, 1H), 3.54 (s, 2H), 3.00-2.89 (m, 2H), 2.14-1.89 (m, 5H), 1.66-1.49 (m, 2H+H2O), 1.04-0.97 (m, 2H), 0.81-0.72 (m, 2H). LC: 98%. MS (EI): m/z 447 (M+H+).

Workup

customthe solvent was evaporated
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-61151663966f4a2c9c1e0af943cca3ec
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000174B2

Reaction notes

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