Hydrochloric Acid → HCID 23320192, compound

HRID 280856Notes

Reaction equation

HRID 280856 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:35][S:36]([Cl:39])(=[O:38])=[O:37].[ClH:40]>C(Cl)(Cl)Cl>[ClH:39].[ClH:40].[CH3:35][S:36]([NH:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[CH2:10][CH2:11][N:12]([CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:13][CH2:14]2)[CH:5]=[CH:4][CH:3]=1)(=[O:38])=[O:37]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 13362831HCID 13362831, compound

Product 1

HCID 23320192HCID 23320192, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1-(6-aminopyridin-2-ylmethyl)-4-benzhydrylpiperazine (3.58 g) and triethylamine (1.01 g) in chloroform (20 ml) was dropwise added methanesulfonylchloride (1.15 g) at 5° to 10° C. under cooling with stirring, which was continued at the same temperature for 1 hour. To the resultant mixture, additional triethylamine (0.51 g) and methanesulfonyl chloride (0.57 g) were added successively. The mixture was stirred for 1.5 hours. The reaction mixture was washed with water, dried and evaporated in vacuo. The resulting oily product was subjected to column chromatography on silica gel eluting with a mixture of chloroform and methanol (30:1). The fractions containing the desired compound were combined and evaporated in vacuo to give a residue. According to a conventional manner, the residue was converted to hydrochloric acid salt, which was recrystallized from a mixture of methanol and diethyl ether to give 1-(6-methanesulfonylaminopyridin-2-ylmethyl)-4-benzhydrylpiperazine dihydrochloride (0.97 g). mp: 201°-202° C.

Workup

  1. customat 5° to 10° C.
  2. temperatureunder cooling
  3. stirringThe mixture was stirred for 1.5 hours
  4. washThe reaction mixture was washed with water
  5. customdried
  6. customevaporated in vacuo
  7. additionThe resulting oily product was subjected to column chromatography on silica gel eluting with a mixture of chloroform and methanol (30:1)
  8. additionThe fractions containing the desired compound
  9. customevaporated in vacuo
  10. customto give a residue
  11. customwas recrystallized from a mixture of methanol and diethyl ether

Sources & evidence

ORD record
ord-806b4c3b9a6d4e78bed737039b1b785a
Source dataset
uspto-grants-1986_05
Patent number
US04591590

Reaction notes

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