Pyridine → N-Benzyl-N-[4-(piperidine-1-carbonyl)-phenyl]-benzenesulfonamide

HRID 2380968Notes

Reaction equation

[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1([S:29](Cl)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.N1C=CC=CC=1>ClCCl>[CH2:1]([N:8]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])=[CH:11][CH:10]=1)[S:29]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:31])=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a stirred solution of (4-benzylamino-phenyl)-piperidin-1-yl-methanone (39 mg, 0.14 mmol) in dichloromethane (1 ml) was added benzene sulfonylchloride (57 μl, 0.46 mmol) followed by pyridine (42 μl, 0.5 mmol) and the reaction was heated to 40° C. for 20 hours. The reaction was allowed to cool to room temperature and partitioned between water (5 ml) and dichloromethane (5 ml). The organics were collected, concentrated in vacuo and purified by preparative TLC to afford the title compound as a white solid (38 mg, 62% yield). HPLC retention time 5.8 min. Mass spectrum (ES+) m/z 435 (M+H).

Workup

temperatureto cool to room temperature
custompartitioned between water (5 ml) and dichloromethane (5 ml)
customThe organics were collected
concentrationconcentrated in vacuo
custompurified by preparative TLC

Sources & evidence

ORD record: ord-0ae7574144b64a72a8ee32e2c53fbef3
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258138B2

Reaction notes

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