Methyl vinyl ketone → 1-{4-[2-(3-Chloro-phenyl)-5-methyl-pyrrol-1-yl]-benzenesulfonyl}-piperidine

HRID 18653

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[CH3:10][C:11](=O)[CH:12]=[CH2:13].[N:15]1([S:21]([C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[N:30]([C:27]3[CH:28]=[CH:29][C:24]([S:21]([N:15]4[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]4)(=[O:23])=[O:22])=[CH:25][CH:26]=3)[C:11]([CH3:10])=[CH:12][CH:13]=2)[CH:7]=[CH:8][CH:9]=1

Participants

Reactant 3

HCID 6570Methyl vinyl ketone

HCID 114773-Chlorobenzaldehyde

HCID 2366484-(Piperidine-1-sulfonyl)aniline

Product 1

HCID 684843231-{4-[2-(3-Chloro-phenyl)-5-methyl-pyrrol-1-yl]-benzenesulfonyl}-piperidine

Procedure

3-Chlorobenzaldehyde and but-3-en-2-one were treated according to the procedure outlined in General Procedure C followed by subjecting the resulting product to conditions outlined in General Procedure D along with p-piperidinylsulfonyl phenylamine to obtain the titled compound. 1H NMR (CDCl3) δ ppm 1.42-1.65 (6H), 2.18 (3H), 3.00 (4H), 6.18 (1H), 6.40 (1H), 6.85-7.90 (8H); MS (ESI) m/z 415 (M+H).

Sources & evidence

ORD record: ord-2d32fddd135b41969e460b8bf3491573
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741364B2

Linked notes

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