Hydrochloric Acid → 2-[3-(Imidazol-1-yl)propylamino]2,2-dimethylethyl benzoate dihydrochloride

HRID 2268251Notes

Reaction equation

HRID 2268251 reaction equation
[C:1]([Cl:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:10]1([CH2:15][CH2:16][CH2:17][NH:18][C:19]([CH3:23])([CH3:22])[CH2:20][OH:21])[CH:14]=[CH:13][N:12]=[CH:11]1.C(=O)(O)[O-].[Na+].[ClH:29]>ClCCl.CCOCC.C(N(CC)CC)C>[ClH:9].[ClH:29].[C:1]([O:21][CH2:20][C:19]([NH:18][CH2:17][CH2:16][CH2:15][N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1)([CH3:23])[CH3:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 183497652-[3-(Imidazol-1-yl)propylamino]-2-methyl-1-propanol

Product 1

HCID 183497172-[3-(Imidazol-1-yl)propylamino]2,2-dimethylethyl benzoate dihydrochloride

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

A solution of benzoyl chloride (0.36 g) in dichloromethane (1.5 ml) was added dropwise to a mixture of 2-[3-(imidazol-1-yl)propylamino]-2-methyl-1-propanol (0.5 g) and triethylamine (0.5 g) in dichloromethane (5 ml) with stirring under nitrogen at 0° C. The mixture was stirred at 0° C. for 1 hour and then allowed to warm up to ambient temperature and stirred at this temperature for 3 hours. Saturated aqueous sodium bicarbonate (5 ml) was added. The mixture was shaken and the organic layer separated. The aqueous layer was extracted with further dichloromethane. The combined organic extracts were dried, filtered and evaporated to give an oil which was dissolved in ether and treated with ethereal hydrogen chloride to give 2-[3-(imidazol-1-yl)propylamino]2,2-dimethylethyl benzoate dihydrochloride, m.p. 198-199° C., after recrystallisation from ethanol.

Workup

  1. stirringThe mixture was stirred at 0° C. for 1 hour
  2. temperatureto warm up to ambient temperature
  3. stirringstirred at this temperature for 3 hours
  4. stirringThe mixture was shaken
  5. customthe organic layer separated
  6. extractionThe aqueous layer was extracted with further dichloromethane
  7. customThe combined organic extracts were dried
  8. filtrationfiltered
  9. customevaporated
  10. customto give an oil which

Sources & evidence

ORD record
ord-9bc1759fd6d64680a97ddc825ae318a3
Source dataset
uspto-grants-2001_12
Patent number
US06326500B1

Reaction notes

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