Hydrochloric Acid → Moricizine hydrochloride

HRID 1590312Notes

Reaction equation

HRID 1590312 reaction equation
[CH3:1][CH2:2][O:3][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]2[S:20][C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]([C:21]([CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:22])[C:11]=2[CH:12]=1)=[O:5].C(O)C.[ClH:34]>>[CH3:1][CH2:2][O:3][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]2[S:20][C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]([C:21]([CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:22])[C:11]=2[CH:12]=1)=[O:5].[ClH:34]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 34633Moricizine2×

Product 1

HCID 34632Moricizine hydrochlorideYield 81%

Conditions

Temperature
72.5 °C

Procedure

To a 250 mL flask equipped with thermometer, condenser, and nitrogen inlet were added 25 grams (0.0585 moles) moricizine and 120 mL (2.048 moles, 35 equivalents) absolute ethanol. The mixture was stirred and heated at 65-80° C. for about 15 minutes, after which time the moricizine was fully dissolved. The heat was turned off and the mixture was allowed to cool with stirring under ambient conditions. When the temperature reached about 35° C., 7.0 grams hydrochloric acid (36.5% HCl, 0.07 moles HCl, 1.2 equivalents HCl) were added. After a precipitate became visible, the mixture was cooled with an ice water bath to about 0° C, maintained at that temperature for about one hour, and then filtered. The solids were dried in a vacuum oven overnight at 50-55° C. to provide 21.98 grams (81% yield) of substantially non-hydrated moricizine hydrochloride. Substantially non-hydrated moricizine hydrochloride was obtained as a white powder having a melt range of 214-217° C., and one strong, sharp peak at about 215° C. on differential scanning calorimetry.

Workup

  1. customTo a 250 mL flask equipped with thermometer, condenser, and nitrogen inlet
  2. temperatureto cool
  3. stirringwith stirring under ambient conditions
  4. customreached about 35° C.
  5. temperaturethe mixture was cooled with an ice water bath to about 0° C
  6. temperaturemaintained at that temperature for about one hour
  7. filtrationfiltered
  8. customThe solids were dried in a vacuum oven overnight at 50-55° C.

Sources & evidence

ORD record
ord-ee26a60cfbab4a0d9e079a18d86abe36
Source dataset
uspto-grants-1993_04
Patent number
US05202435

Reaction notes

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