Hydrochloric Acid → HCID 19429378, compound

HRID 1078371Notes

Reaction equation

HRID 1078371 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=O)[CH3:2].[NH2:10][CH2:11][CH2:12][CH2:13][N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1.[ClH:19].C([BH3-])#N.[Na+].C[OH:25]>O.C(OCC)C>[ClH:19].[ClH:19].[Cl:19][C:7]1[CH:6]=[CH:5][C:4]([CH:1]([NH:10][CH2:11][CH2:12][CH2:13][N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)[CH3:2])=[C:9]([OH:25])[CH:8]=1

Participants

8

Reactant 5

HCID 313Hydrochloric Acid3×HCID 887MethanolHCID 7410AcetophenoneHCID 787361H-Imidazole-1-propanamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 19429378HCID 19429378, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

The acetophenone (3.3 g) from (b) and 1-(3-aminopropyl)imidazole (7.1 g) were dissolved in methanol (30 ml). Saturated methanolic hydrogen chloride (3 ml) was added to this solution, followed by sodium cyanoborohydride (0.84 g). The resulting mixture was stirred at ambient temperature for 48 hours and then left standing for 64 hours. Concentrated hydrochloric acid (6 ml) and water (30 ml) were added and the mixture stirred for 10 minutes. The mixture was diluted with water, washed with dichloromethane, basified with 5M sodium hydroxide solution and then extracted with dichloromethane. The combined extracts were dried and evaporated to give an oil which was dissolved in diethyl ether and acidified with ethereal hydrogen chloride. The solid obtained was collected by filtration and dried under vacuum to give 5-chloro-2-{1-[3-(imidazol-1-yl)propylamino]ethyl}phenol dihydrochloride, m.p. >300° C.

Workup

  1. waitleft
  2. waitstanding for 64 hours
  3. stirringthe mixture stirred for 10 minutes
  4. washwashed with dichloromethane
  5. extractionextracted with dichloromethane
  6. customThe combined extracts were dried
  7. customevaporated
  8. customto give an oil which
  9. customThe solid obtained
  10. filtrationwas collected by filtration
  11. customdried under vacuum

Sources & evidence

ORD record
ord-b19f533b56754b94ab67b8269fa595ab
Source dataset
uspto-grants-1996_08
Patent number
US05547972

Reaction notes

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