1-(1H-1,3-benzodiazol-2-yl)propan-1-amine → 1-(4-Benzyloxyphenyl)-2-[3-(1-benzimidazolyl)-propylamino]-ethanol

HRID 355198Notes

Reaction equation

HRID 355198 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)=[O:4].NC([C:23]1[NH:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=1)CC.[BH4-].[Na+]>C(#N)C>[CH2:12]([O:11][C:8]1[CH:9]=[CH:10][C:5]([CH:3]([OH:4])[CH2:2][NH:24][CH2:25][CH2:26][CH2:28][N:24]2[C:25]3[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=3[N:27]=[CH:23]2)=[CH:6][CH:7]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 27719961-(1H-1,3-benzodiazol-2-yl)propan-1-amineHCID 4311764Sodium borohydrideHCID 105425931-[4-(Benzyloxy)phenyl]-2-bromoethan-1-one

Product 1

HCID 202149221-(4-Benzyloxyphenyl)-2-[3-(1-benzimidazolyl)-propylamino]-ethanol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

30.5 gm of 2-bromo-p-benzyloxyacetophenone and 35 gm of 1-aminopropyl-benzimidazole were stirred for 1 hour at 30°-40° C. in 150 ml of acetonitrile. After separation of the hydrobromide, the mother liquor was acidified with 12 gm of maleic acid, and the precipitated α-[3-(1-benzimidazolyl)propylamino]-4-benzyloxyacetophenone maleate (m.p. 145°-148° C.) was collected by suction of filtiation. Aqueous ammonia was used to prepare the base, which was reduced in 200 ml of alcohol with sodium borohydride to form 1-(4-benzyloxyphenyl)-2-[3-(1-benzimidazolyl)-propylamino]-ethanol (m.p. 83°-85° C.).

Workup

  1. customAfter separation of the hydrobromide
  2. customthe precipitated α-[3-(1-benzimidazolyl)propylamino]-4-benzyloxyacetophenone maleate (m.p. 145°-148° C.) was collected by suction of filtiation
  3. customto prepare the base, which

Sources & evidence

ORD record
ord-910f48810ded4cf09b020644e3728bfb
Source dataset
uspto-grants-1983_03
Patent number
US04378361

Reaction notes

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