Hydrogen Bromide → 1-[1-(2-aminoethyl)-4-piperidinyl]-5-chloro-1,3-dihydro-2H-benzimidazol-2-one dihydrobromide

HRID 437655Notes

Reaction equation

HRID 437655 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][NH:18]C(=O)OCC)[CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[BrH:26]>O>[BrH:26].[BrH:26].[NH2:18][CH2:17][CH2:16][N:13]1[CH2:14][CH2:15][CH:10]([N:6]2[C:5]3[CH:24]=[CH:25][C:2]([Cl:1])=[CH:3][C:4]=3[NH:8][C:7]2=[O:9])[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 54131181ethyl {2-[4-(5-chloro-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]-ethyl}carbamate

Product 1

HCID 214289771-[1-(2-aminoethyl)-4-piperidinyl]-5-chloro-1,3-dihydro-2H-benzimidazol-2-one dihydrobromide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 6.6 parts of ethyl {2-[4-(5-chloro-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]ethyl }-carbamate, 60 parts of a hydrobromic acid solution 48% in water and 4 parts of water is stirred and refluxed for 2.50 hours. After cooling, the precipitated product is filtered off and crystallized from water, yielding 5.5 parts of 1- [1-(2-aminoethyl)-4-piperidinyl]-5-chloro-1,3-dihydro-2H-benzimidazol-2-one dihydrobromide; mp. > 300° C.

Workup

  1. temperaturerefluxed for 2.50 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitated product is filtered off
  4. customcrystallized from water

Sources & evidence

ORD record
ord-fdb8cc3a06df400a90ddad83698fad93
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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