Tetrahydrofuran → (4-Isopropyl-piperazin-1-yl)-(4-morpholin-4-ylmethyl-phenyl)-methanone Mono-fumarate Salt

HRID 560976Notes

Reaction equation

HRID 560976 reaction equation
C1COCC1.[CH:6]([N:9]1[CH2:14][CH2:13][N:12]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:19][CH:18]=2)=[O:16])[CH2:11][CH2:10]1)([CH3:8])[CH3:7].[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34]>CCO>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34].[CH:6]([N:9]1[CH2:14][CH2:13][N:12]([C:15]([C:17]2[CH:18]=[CH:19][C:20]([CH2:23][N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)=[CH:21][CH:22]=2)=[O:16])[CH2:11][CH2:10]1)([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 444972Fumaric AcidHCID 10042344(4-Isopropyl-piperazin-1-yl)-(4-morpholin-4-ylmethyl-phenyl)-methanone2×

Product 1

HCID 86612815(4-Isopropyl-piperazin-1-yl)-(4-morpholin-4-ylmethyl-phenyl)-methanone Mono-fumarate Salt

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a THF solution (40 mL) of (4-isopropyl-piperazin-1-yl)-(4-morpholin-4-ylmethyl-phenyl)-methanone (3.0 g, 9.0 mmol) were added THF (40 mL) and fumaric acid (3.3 g, 28.4 mmol). The resulting mixture was heated to 60° C. and stirred for 0.5 h. The resulting suspension was cooled to 0° C. and the resulting precipitate was collected by filtration, washed with THF (20 mL), and dried in a vacuum oven at 65° C. for 20 h to yield crude title compound as a white solid. A suspension of crude (4-isopropyl-piperazin-1-yl)-(4-morpholin-4-ylmethyl-phenyl)-methanone, mono-fumarate (5.7 g, 12.7 mmol) in absolute EtOH (110 mL) was heated to 70° C. Any insoluble material was removed by filtration through a Celite pad. The filtrate was reheated to 65° C. and then cooled to 0° C. The precipitate was collected by filtration and washed with MTBE (20 mL). The solids were dried in a vacuum oven at 65° C. for 20 h to yield the title compound as a white solid.

Workup

  1. temperatureThe resulting suspension was cooled to 0° C.
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with THF (20 mL)
  4. customdried in a vacuum oven at 65° C. for 20 h
  5. customto yield crude title compound as a white solid
  6. temperaturewas heated to 70° C
  7. customAny insoluble material was removed by filtration through a Celite pad
  8. customwas reheated to 65° C.
  9. temperaturecooled to 0° C
  10. filtrationThe precipitate was collected by filtration
  11. washwashed with MTBE (20 mL)
  12. customThe solids were dried in a vacuum oven at 65° C. for 20 h

Sources & evidence

ORD record
ord-de0c930d79534a5ca4e93175238f55cf
Source dataset
uspto-grants-2011_11
Patent number
US08063206B2

Reaction notes

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