Acetic Acid → 1-Cyclohexyl-4-(4-(2-methoxyphenyl)piperazin-1-yl)-2-methyl-2-phenylbutan-1-one

HRID 496905Notes

Reaction equation

HRID 496905 reaction equation
[C:1]1([C:7]([C:12]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:13])([CH3:11])[CH2:8][CH:9]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]1[CH2:34][CH2:33][N:32]([CH2:9][CH2:8][C:7]([C:12]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:13])([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH3:11])[CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 9899402N-(2-Methoxyphenyl)piperazine hydrochlorideHCID 117801924-Cyclohexyl-3-methyl-4-oxo-3-phenylbutanal

Product 1

HCID 98029871-Cyclohexyl-4-(4-(2-methoxyphenyl)piperazin-1-yl)-2-methyl-2-phenylbutan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Phenyl-3-cyclohexanecarbonylbutan-1-al (57.8 g, 224 mmol) was dissolved in methylene chloride (1650 mL) followed by addition of 1-(2-methoxyphenyl)piperazine hydrochloride (56.3 g, 246 mmol). Acetic acid (41 mL) may optionally be added to turn the slurry into a solution. To the stirred solution, sodium triacetoxyborohydride (60.3 g, 284 mmol) was slowly added. A slight exotherm resulted and a slurry was produced. The reaction mixture was stirred for an additional 3 hours at room temperature. The reaction was then quenched by addition of 2.0 N sodium hydroxide (1050 mL) producing a pH of about 10 for the quenched reaction mixture. The mixture was then extracted with methylene chloride (2 times, 1L and 300 mL) The organic extracts were combined, washed successively with 1.0 N HCl (600 mL), 1.0 N sodium hydroxide (600 mL), brine (600 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to provide the final title compound as a thick oil;

Workup

  1. customA slight exotherm resulted
  2. customa slurry was produced
  3. customThe reaction was then quenched by addition of 2.0 N sodium hydroxide (1050 mL)
  4. customproducing a pH of about 10
  5. customfor the quenched reaction mixture
  6. extractionThe mixture was then extracted with methylene chloride (2 times, 1L and 300 mL) The organic extracts
  7. washwashed successively with 1.0 N HCl (600 mL), 1.0 N sodium hydroxide (600 mL), brine (600 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-551808bb110043eea8ba095ccc19549f
Source dataset
uspto-grants-2005_09
Patent number
US06946579B2

Reaction notes

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