3-Cyanobenzene-1-sulfonyl chloride → cis-1-(3-Cyanobenzenesulphonyl)-2,6-dimethyl-4-phenylmethylpiperazine

HRID 1064596Notes

Reaction equation

HRID 1064596 reaction equation
[CH2:1]([N:8]1[CH2:13][C@@H:12]([CH3:14])[NH:11][C@@H:10]([CH3:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]([C:18]1[CH:19]=[C:20]([S:24](Cl)(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1)#[N:17]>N1C=CC=CC=1>[C:16]([C:18]1[CH:19]=[C:20]([S:24]([N:11]2[C@H:10]([CH3:15])[CH2:9][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:13][C@@H:12]2[CH3:14])(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1)#[N:17]

Participants

4

Reactant 2

HCID 28013603-Cyanobenzene-1-sulfonyl chlorideHCID 12197174(3r,5s)-1-Benzyl-3,5-dimethylpiperazine

Product 1

HCID 69746861cis-1-(3-Cyanobenzenesulphonyl)-2,6-dimethyl-4-phenylmethylpiperazine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of cis-4-benzyl-2,6-dimethylpiperazine (1 g), 4-N,N-dimethylaminopyridine(0.54 g), 3-cyanobenzenesulphonyl chloride (2.13 g) in pyridine (3 ml) were stirred at ambient temperature. After 1 h the mixture was partitioned between dichloromethane and water. The organic phase further washed with brine, collected, dried, (MgSO4) and solvent evaporated under reduced pressure to leave the subtitle compound as an orange gum. Yield: 1 g

Workup

  1. customAfter 1 h the mixture was partitioned between dichloromethane and water
  2. washThe organic phase further washed with brine
  3. customcollected
  4. customdried
  5. custom(MgSO4) and solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-d447eb12e2d34832b0a79827c2d5c615
Source dataset
uspto-grants-2005_11
Patent number
US06969713B2

Reaction notes

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