Hydrochloric Acid → HCID 15563248, compound

HRID 1042555Notes

Reaction equation

HRID 1042555 reaction equation
[CH3:1][C:2]1[N:6]2[C:7]3[CH:8]=[CH:9][C:10]([Cl:23])=[CH:11][C:12]=3[C:13]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=3[F:22])=[N:14][CH2:15][C:5]2=[CH:4][N:3]=1.C(O)C.[ClH:27]>C(O)(C)C>[ClH:23].[ClH:27].[Cl:23][C:10]1[CH:9]=[CH:8][C:7]2[N:6]3[C:2]([CH3:1])=[N:3][CH:4]=[C:5]3[CH2:15][N:14]=[C:13]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=3[F:22])[C:12]=2[CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 4192Midazolam

Product 1

HCID 15563248HCID 15563248, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
30 °C

Procedure

A 4-neck RBF was charged under nitrogen flow with: 1 g of Midazolam (IV) (prepared according to example 2) and 15 mL of Ethanol. The slurry was stirred until complete dissolution at 25/30° C. 5 mL of a ethanolic solution of Hydrochloric acid 2N were slowly added. 20 mL of Isopropanol were added over 30 minutes at RT. The slurry was cooled down at −15° C. in one hour and kept at that temperature for at least 2 hours. The slurry was then filtered and the cake was washed with 10 mL of cool isopropanol. The filter was discharged and the product was dried at 40° C. under vacuum for 2 hours and then at 60° C. for 8 hours. Midazolam dihydrochloride as white solid was collected.

Workup

  1. temperatureThe slurry was cooled down at −15° C. in one hour
  2. waitkept at that temperature for at least 2 hours
  3. filtrationThe slurry was then filtered
  4. washthe cake was washed with 10 mL of cool isopropanol
  5. customthe product was dried at 40° C. under vacuum for 2 hours
  6. customMidazolam dihydrochloride as white solid was collected

Sources & evidence

ORD record
ord-2d94d26cf9824f93ab20389650018ccf
Source dataset
uspto-grants-2013_10
Patent number
US08557981B2

Reaction notes

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