Hydrogen Bromide → N-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl][1,4'-bipiperidine]-4-amine

HRID 620485Notes

Reaction equation

HRID 620485 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]([CH:25]3[CH2:30][CH2:29][N:28](C(OCC)=O)[CH2:27][CH2:26]3)[CH2:21][CH2:20]2)=[CH:4][CH:3]=1.Br>>[F:1][C:2]1[CH:3]=[CH:4][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]([CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[CH2:21][CH2:20]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 13588068ethyl 4-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-ylamino][1,4'-bipiperidine]-1'-carboxylate

Product 1

HCID 15614720N-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl][1,4'-bipiperidine]-4-amineYield 50%

Procedure

A mixture of 21 parts of ethyl 4-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-ylamino][1,4'-bipiperidine]-1'-carboxylate and 450 parts of hydrobromic acid solution 48% was stirred and refluxed for 16 hours. The reaction mixture was evaporated. From the residue the free base was liberated in the conventional manner with sodium hydroxide in water and extracted with dichloromethane. The extract was dried, filtered and evaporated, yielding 8 parts (50%) of N-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl][1,4'-bipiperidine]-4-amine as a residue (intermediate 71).

Workup

  1. temperaturerefluxed for 16 hours
  2. customThe reaction mixture was evaporated
  3. extractionextracted with dichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-6588eb6059414d2aaabf7911c0505f42
Source dataset
uspto-grants-1989_04
Patent number
US04820822

Reaction notes

Loading…