Sodium Carbonate → Bavisant

HRID 1367615Notes

Reaction equation

HRID 1367615 reaction equation
Cl.Cl.[CH:3]1([N:6]2[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:5][CH2:4]1.[OH-].[Na+].C([O-])([O-])=O.[Na+].[Na+].[N:20]1([CH2:26][C:27]2[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>C1(C)C=CC=CC=1>[CH:3]1([N:6]2[CH2:11][CH2:10][N:9]([C:31]([C:30]3[CH:29]=[CH:28][C:27]([CH2:26][N:20]4[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)=[CH:35][CH:34]=3)=[O:32])[CH2:8][CH2:7]2)[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 137489614-Morpholin-4-ylmethyl-benzoyl chlorideHCID 212208121-Cyclopropylpiperazine dihydrochloride

Product 1

HCID 16061509Bavisant

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A 250 mL, two-neck flask fitted with an addition funnel and thermocouple probe was charged with 1-cyclopropyl-piperazine dihydrochloride (7.1 g, 0.036 mol, 1.0 eq) and toluene (70 mL) and then cooled to 0° C. Aqueous NaOH solution (1.0 M, 70 mL, 2.0 eq) was added at such a rate that the reaction temperature did not exceed 10° C. Na2CO3 powder (7.5 g, 0.071 mol, 2.0 eq) was then added to the reaction mixture. The 4-morpholin-4-ylmethyl-benzoyl chloride, prepared as in Step A above (9.8 g, 0.036 mol, 1.0 eq) was added in portions over 3 minutes, while the temperature of the reaction mixture was maintained below 5° C. The reaction mixture was then stirred for 2 hrs. The reaction mixture was filtered, the layers were separated, the aqueous layer was extracted with toluene (30 mL×2), and the combined organic layers washed with brine (30 mL) and dried over Na2SO4. The solvent was removed in vacuo to yield the title compound as a as pale yellow viscous oil.

Workup

  1. customA 250 mL, two-neck flask fitted with an addition funnel
  2. customdid not exceed 10° C
  3. additionwas added in portions over 3 minutes, while the temperature of the reaction mixture
  4. temperaturewas maintained below 5° C
  5. filtrationThe reaction mixture was filtered
  6. customthe layers were separated
  7. extractionthe aqueous layer was extracted with toluene (30 mL×2)
  8. washthe combined organic layers washed with brine (30 mL)
  9. dry with materialdried over Na2SO4
  10. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-02174e1573074755b6ca29a81069b238
Source dataset
uspto-grants-2011_02
Patent number
US07893257B2

Reaction notes

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