Methanesulfonyl chloride → HCID 23320188, compound

HRID 280855Notes

Reaction equation

HRID 280855 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1.[CH3:28][S:29](Cl)(=[O:31])=[O:30].[C:33]([O-:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([O-:38])=[O:37]>N1C=CC=CC=1.C(Cl)(Cl)Cl>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37].[CH3:28][S:29]([NH:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[CH2:5][N:6]1[CH2:7][CH2:8][N:9]([CH:12]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:10][CH2:11]1)(=[O:31])=[O:30]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 5460307FumarateHCID 13362832HCID 13362832, compound

Product 1

HCID 23320188HCID 23320188, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 1-(3-aminobenzyl)-4-benzhydrylpiperazine (1.43 g) in a mixture of pyridine (3.2 g) and chloroform (20 ml) was dropwise added methanesulfonylchloride (0.31 ml) at 5° to 6° C. with stirring. The mixture was stirred at the same temperature for 30 minutes and at ambient temperature for 2 hours. The reaction mixture was concentrated and the resultant was extracted with ethyl acetate. The extract was washed with water, dried and evaporated in vacuo to give a residue. According to a conventional manner, the residue was converted to fumarate, which was recrystallized from ethanol to afford 1-(3-methanesulfonylaminobenzyl)-4-benzhydrylpiperazine fumarate (0.65 g) as yellow crystals. mp: 213°-215° C.

Workup

  1. customat 5° to 6° C.
  2. stirringThe mixture was stirred at the same temperature for 30 minutes and at ambient temperature for 2 hours
  3. concentrationThe reaction mixture was concentrated
  4. extractionthe resultant was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. customevaporated in vacuo
  8. customto give a residue
  9. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-892c9eac1a6845d1a821c8e27435dd6d
Source dataset
uspto-grants-1986_05
Patent number
US04591590

Reaction notes

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