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

HRID 378624Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 378624
[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

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-98655d194b8d473187f126afff09e616
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06031109

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