Hydrogen Bromide → Norastemizole hydrobromide

HRID 1762818Notes

Reaction equation

HRID 1762818 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[NH:18][CH:19]2[CH2:24][CH2:23][N:22](C(OCC)=O)[CH2:21][CH2:20]2)=[CH:4][CH:3]=1.[BrH:30]>>[BrH:30].[BrH:30].[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[NH:18][CH:19]2[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 3019916Ethyl 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-YL]amino]piperidine-1-carboxylate

Product 1

HCID 3018631Norastemizole hydrobromideYield 82%

Procedure

A mixture of 3.2 parts of ethyl 4-[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-ylamino]-1-piperidinecarboxylate and 300 parts of hydrobromic acid solution 48% was stirred and refluxed for 1 hour. The reaction mixture was evaporated and the residue was crystallized from 2-propanol. The product was filtered off and dried, yielding 3.3 parts (82%) of 1-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-amine dihydrobromide; mp. 290.2° C. (compound 112).

Workup

  1. temperaturerefluxed for 1 hour
  2. customThe reaction mixture was evaporated
  3. customthe residue was crystallized from 2-propanol
  4. filtrationThe product was filtered off
  5. customdried

Sources & evidence

ORD record
ord-ee495493cc6a4a81b0e1fa4b82a474b8
Source dataset
uspto-grants-1989_05
Patent number
US04835161

Reaction notes

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