Water → HCID 23142177, compound

HRID 2218857Notes

Reaction equation

HRID 2218857 reaction equation
[CH3:1][C:2]1([CH3:26])[CH2:7][CH2:6][CH:5]([C:8]2[CH:9]=[C:10]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[CH:11]=[CH:12][C:13]=2[N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:34][C:35](=[O:38])[CH2:36][CH3:37].O>CN(C)C=O.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:26])[CH2:3][CH2:4][CH:5]([C:8]2[CH:9]=[C:10]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[CH:11]=[CH:12][C:13]=2[N:14]2[CH2:15][CH2:16][N:17]([CH2:34][C:35](=[O:38])[CH2:36][CH3:37])[CH2:18][CH2:19]2)[CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 131561-Bromo-2-butanoneHCID 23141750HCID 23141750, compound

Product 1

HCID 23142177HCID 23142177, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-[3-(4,4-dimethylcyclohexyl)-4-piperazin-1-ylphenyl]morpholine (20 mg, 0.052 mmol) produced in Example (84b) in dimethylformamide (1 mL) were added potassium carbonate (11 mg, 0.078 mmol) and 1-bromo-2-butanone (9.4 mg, 0.063 mmol), followed by stirring for 2 hours and 5 minutes at an external temperature of 80° C. After air-cooling, water was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with water and then filtered through Celite, and the filtrate was concentrated. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 1-[4-[2-(4,4-dimethylcyclohexyl)-4-morpholin-4-ylphenyl]piperazin-1-yl]butan-2-one. This compound was dissolved in ethyl acetate, and a 4N solution of hydrogen chloride in ethyl acetate (0.020 mL, 0.080 mmol) was added. The solution was concentrated under reduced pressure, and then hexane was added to the obtained residue to produce a solid. The solid was triturated by sonication and the supernatant hexane solution was removed. The obtained solid residue was dried under reduced pressure to give 25 mg of the title compound as a white solid.

Workup

  1. temperatureAfter air-cooling
  2. washThe organic layer was washed with water
  3. filtrationfiltered through Celite
  4. concentrationthe filtrate was concentrated
  5. customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-ec1a13a4235040618ed545b774936cbc
Source dataset
uspto-grants-2008_08
Patent number
US07410971B2

Reaction notes

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