4-Chlorobenzenesulfonyl chloride → 1H-1,4-Diazepine, 1-[(4-chlorophenyl)sulfonyl]hexahydro-

HRID 2289537Notes

Reaction equation

HRID 2289537 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH:12]1[CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:12]2[CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 68163Hexahydro-1,4-diazepine

Product 1

HCID 116087901H-1,4-Diazepine, 1-[(4-chlorophenyl)sulfonyl]hexahydro-Yield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The 1-(4-chlorophenylsulphonyl)homopiperazine was prepared as follows. 4-Chlorophenylsulphonyl chloride (3.74 g) in dichloromethane (100 ml) was added slowly to a solution of homopiperazine (6.73 g) in dichloromethane (100 ml). The reaction was stood at room temperature overnight. The reaction was washed with water, dried (MgSO4) and the solvent removed in vacuo. The residue was triturated with 20% ether in hexane to give 1-(4-chlorophenylsulphonyl)homopiperazine (3.71 g); NMR (DMSOd6): 1.65 (m, 2H), 2.73 (m, 4H), 3.2-3.65 (m 4H), 7.7 (m, 2H), 7.8 (m, 2H).

Workup

  1. customThe 1-(4-chlorophenylsulphonyl)homopiperazine was prepared
  2. washThe reaction was washed with water
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customThe residue was triturated with 20% ether in hexane

Sources & evidence

ORD record
ord-1286599c27e44beaa45237ffe2c7afa0
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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