tert-Butyl methyl ether → 1-(2-Methoxyphenyl)-4-[3-(cyclohexanecarbonyl)-3-(phenyl)butyl]piperazine maleate

HRID 496906Notes

Reaction equation

HRID 496906 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]([C:25]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[O:26])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:18])[CH2:11][CH2:10]1.[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37].CC(OC)(C)C>CO>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][C:17]([C:25]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[O:26])([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH3:18])[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 444266Maleic AcidHCID 98029871-Cyclohexyl-4-(4-(2-methoxyphenyl)piperazin-1-yl)-2-methyl-2-phenylbutan-1-one

Product 1

HCID 694195741-(2-Methoxyphenyl)-4-[3-(cyclohexanecarbonyl)-3-(phenyl)butyl]piperazine maleate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(2-Methoxyphenyl)-4-[3-(cyclohexanecarbonyl)-3-(phenyl)butyl]piperazine (prepared directly above) was dissolved in warm methanol (50 mL) followed by addition of maleic acid (26.8 g) and MTBE (200 mL). This mixture was concentrated to a paste and then redissolved by addition of methanol (approximately 15 mL) and MTBE (200 mL). The mixture was seeded and an additional amount of MTBE (300 mL) was added once crystallization was initiated. The mixture was suction filtered, and the solid rinsed with MTBE and vacuum dried for 5 hours at 40° C. to provide the title compound (122 g).

Workup

  1. concentrationThis mixture was concentrated to a paste
  2. dissolutionredissolved by addition of methanol (approximately 15 mL) and MTBE (200 mL)
  3. additionan additional amount of MTBE (300 mL) was added once
  4. customcrystallization
  5. filtrationfiltered
  6. washthe solid rinsed with MTBE and vacuum
  7. customdried for 5 hours at 40° C.

Sources & evidence

ORD record
ord-0f246e1c31f74286bca6096f2a8c4b6e
Source dataset
uspto-grants-2005_09
Patent number
US06946579B2

Reaction notes

Loading…