Benzenesulfonyl chloride → 1-Benzenesulfonyl-4-[4-(3-piperidin-1-yl-propoxy)-benzyl]-[1,4]diazepane

HRID 1434579Notes

Reaction equation

HRID 1434579 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:24]=[CH:23][C:14]([CH2:15][N:16]3[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:25]1([S:31](Cl)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CC(=O)CC.CO>[C:25]1([S:31]([N:19]2[CH2:20][CH2:21][CH2:22][N:16]([CH2:15][C:14]3[CH:23]=[CH:24][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)=[CH:12][CH:13]=3)[CH2:17][CH2:18]2)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 596405921-[4-(3-Piperidin-1-yl-propoxy)-benzyl]-[1,4]diazepane

Product 1

HCID 579357131-Benzenesulfonyl-4-[4-(3-piperidin-1-yl-propoxy)-benzyl]-[1,4]diazepaneYield 64.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

1-[4-(3-Piperidin-1-yl-propoxy)-benzyl]-[1,4]diazepane (D4) (100 mg, 0.30 mmol) was dissolved in 2-butanone (5 ml), treated with benzene sulfonyl chloride (57 mg, 0.32 mmol) and allowed to stir at room temperature under argon for 2 hours. The reaction mixture was diluted with methanol and passed down an SCX column (2 g) eluting with methanol followed by ammonia/methanol (1:9). The basic fractions were combined and concentrated in vacuo to afford the title compound (91 mg). MS(ES+) m/e 472 [M+H]+.

Workup

  1. washeluting with methanol
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b3559da8db224e8c883deec920018295
Source dataset
uspto-grants-2009_11
Patent number
US07615550B2

Reaction notes

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