4-Methoxybenzenesulfonyl chloride → HCID 86594086, compound

HRID 348545Notes

Reaction equation

HRID 348545 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][CH:10]2[CH2:15][CH2:14][N:13]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]3=[O:22])[CH2:12][CH2:11]2)[CH:6]=[CH:7][CH:8]=1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]([CH:10]2[CH2:11][CH2:12][N:13]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]3=[O:22])[CH2:14][CH2:15]2)[S:31]([C:28]2[CH:27]=[CH:26][C:25]([O:24][CH3:23])=[CH:30][CH:29]=2)(=[O:33])=[O:32])[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 86594087HCID 86594087, compound

Product 1

HCID 86594086HCID 86594086, compound

Procedure

The title compound, MS (ISP): m/e=551.4 (M+H+), was prepared as for example 99, steps (A) to (F). Step (B) was performed using 3-methoxy-aniline, and yielded (+/−)-trans-2-[4-(3-methoxy-phenylamino)-piperidin-1-yl]-cyclohexanol, which was oxidized to (+/−)-2-[4-(3-methoxy-phenylamino)-piperidin-1-yl]-cyclohexanone in step (C). This was then reacted with 4-methoxy-benzensulfonyl chloride in step (D), yielding (+/−)-N-(3-methoxy-phenyl)-4-methoxy-N-[1-(2-oxo-cyclohexyl)-piperidin-4-yl]-benzenesulfonamide. The final step (F) was performed with bromobenzene.

Sources & evidence

ORD record
ord-892f3bfea4894021a6b75459de5b486d
Source dataset
uspto-grants-2007_02
Patent number
US07176316B2

Reaction notes

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