Hydrochloric Acid → Enerisant hydrochloride

HRID 1928665Notes

Reaction equation

HRID 1928665 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[C:20]([C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[O:23])[CH:19]=[N:18]2)=[CH:13][CH:12]=1.[ClH:30]>C(OCC)(=O)C.C(O)C>[ClH:30].[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[C:20]([C:22]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)=[O:23])[CH:19]=[N:18]2)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 42601503Enerisant

Product 1

HCID 66933564Enerisant hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 4-{[1-(4-{3-[(2R)-2-methylpyrrolidin-1-yl]propoxy}phenyl)-1H-pyrazol-4-yl]carbonyl}morpholine obtained in Example 6-(2) (2.62 g) in ethyl acetate (18 mL), a solution of hydrochloric acid in ethyl acetate (4 M, 2.46 mL) was added and stirred at room temperature for 30 minutes. The precipitated crystal was collected by filtration to give a crude crystal (2.9 g). A suspension of the resulting crude crystal in ethanol (9 mL) was heated under reflux to give a solution, which was then filtered. After addition of ethanol (6 mL), the filtrate was stirred for 30 minutes while cooling to room temperature. The mixture was further stirred in an ice bath for 1.5 hours, and the precipitated crystal was collected by filtration and dried to give the titled compound (2.67 g) as a colorless powder.

Workup

  1. filtrationThe precipitated crystal was collected by filtration
  2. customto give a crude crystal (2.9 g)
  3. temperaturewas heated
  4. temperatureunder reflux
  5. customto give a solution, which
  6. filtrationwas then filtered
  7. additionAfter addition of ethanol (6 mL)
  8. stirringthe filtrate was stirred for 30 minutes
  9. temperaturewhile cooling to room temperature
  10. stirringThe mixture was further stirred in an ice bath for 1.5 hours
  11. filtrationthe precipitated crystal was collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-d593990c1f3d46b5a4c4f4aad7de74bd
Source dataset
uspto-grants-2012_05
Patent number
US08183387B2

Reaction notes

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