Hydrogen Bromide → N-[1-(2-aminoethyl)-4-piperidinyl]-1-(4-thiazolylmethyl)-1H-benzimidazol-2-amine trihydrobromide

HRID 845783Notes

Reaction equation

HRID 845783 reaction equation
[S:1]1[CH:5]=[C:4]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[NH:16][CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][NH:25]C(=O)OCC)[CH2:19][CH2:18]2)[N:3]=[CH:2]1.[BrH:31]>O>[BrH:31].[BrH:31].[BrH:31].[NH2:25][CH2:24][CH2:23][N:20]1[CH2:19][CH2:18][CH:17]([NH:16][C:8]2[N:7]([CH2:6][C:4]3[N:3]=[CH:2][S:1][CH:5]=3)[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=2)[CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 15614723ethyl [2-[4-[[1-(4-thiazolylmethyl)-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]carbamate

Product 1

HCID 15614725N-[1-(2-aminoethyl)-4-piperidinyl]-1-(4-thiazolylmethyl)-1H-benzimidazol-2-amine trihydrobromide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 14 parts of ethyl [2-[4-[[1-(4-thiazolylmethyl) -1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]carbamate and 300 parts of a hydrobromic acid solution 48% in water was stirred and refluxed for 30 minutes. The reaction mixture was evaporated. The sticky residue solidified in a mixture of ethanol and acetonitrile. The product was filtered off and dried, yielding 14 parts of N-[1-(2-aminoethyl)-4-piperidinyl]-1-(4-thiazolylmethyl) -1H-benzimidazol-2-amine trihydrobromide (intermediate 134).

Workup

  1. temperaturerefluxed for 30 minutes
  2. customThe reaction mixture was evaporated
  3. additionThe sticky residue solidified in a mixture of ethanol and acetonitrile
  4. filtrationThe product was filtered off
  5. customdried

Sources & evidence

ORD record
ord-42f63d022f76458b92fe3b42e15f50da
Source dataset
uspto-grants-1988_07
Patent number
US04760074

Reaction notes

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