Triethylamine → HCID 57664577, compound

HRID 1467866Notes

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.Br[CH2:28][C:29]1[CH:38]=[CH:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[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:38]=[CH:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[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 2-bromomethyl-naphthalene (88 mg, 0.4 mmol). The reaction mixture was stirred for 12 hours at 80° C. and then the solvent was evaporated. The residue was purified by flash chromatography to give 12.8 mg of the desired product N-cyclopropyl-N-[1-(naphth-2-ylmethyl)-piperidin-4-yl]benzenesulfonamide (15). 1H NMR (CDCl3): δ 8.06-7.71 (m, 7H), 7.61-7.44 (m, 5H), 3.94-3.84 (m, 1H), 3.68 (S, 2H), 3.01-2.94 (m, 2H), 2.18-1.94 (m, 5H), 1.58-1.49 (m, 2H), 1.02-0.96 (m, 2H), 0.81-0.74 (m, 2H). MS (EI): m/z 421 (M+H+).

Workup

customthe solvent was evaporated
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-39e5609e1ae447f3bed8e995e05cc9f2
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000174B2

Reaction notes

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