Thionyl Chloride → N-[1-(2-chloroethyl)-4-piperidinyl]-1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine dihydrochloride

HRID 1856572Notes

Reaction equation

HRID 1856572 reaction equation
S(Cl)([Cl:3])=O.[ClH:5].Cl.[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]=[C:16]2[NH:24][CH:25]2[CH2:30][CH2:29][N:28]([CH2:31][CH2:32]O)[CH2:27][CH2:26]2)=[CH:10][CH:9]=1>ClC(Cl)Cl>[ClH:3].[ClH:5].[Cl:5][CH2:32][CH2:31][N:28]1[CH2:29][CH2:30][CH:25]([NH:24][C:16]2[N:15]([CH2:14][C:11]3[CH:12]=[CH:13][C:8]([F:7])=[CH:9][CH:10]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]=2)[CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 679186284-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-ylamino]-1-piperidineethanol dihydrochloride

Product 1

HCID 12891728N-[1-(2-chloroethyl)-4-piperidinyl]-1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine dihydrochlorideYield 83%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 15 parts of thionyl chloride, 4 parts of 4-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-ylamino]-1-piperidineethanol dihydrochloride and 375 parts of trichloromethane is stirred and refluxed overnight. The precipitated product is filtered off and dried, yielding 13 parts (83%) of N-[1-(2-chloroethyl)-4-piperidinyl]-1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine dihydrochloride; mp.>260° C.

Workup

  1. temperaturerefluxed overnight
  2. filtrationThe precipitated product is filtered off
  3. customdried

Sources & evidence

ORD record
ord-85c2277588b944a4a117081087fc24b1
Source dataset
uspto-grants-1980_08
Patent number
US04219559

Reaction notes

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