Acetic Acid → 1-[2-(4,4-Dimethylcyclohex-1-enyl)-5-methoxyphenyl]-4-pentylpiperazine

HRID 32135

Reaction equation

HRID 32135 reaction equation
[CH3:1][C:2]1([CH3:22])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=2[N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:4][CH2:3]1.[CH:23](=O)[CH2:24][CH2:25][CH2:26][CH3:27].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:1][C:2]1([CH3:22])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=2[N:16]2[CH2:21][CH2:20][N:19]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:18][CH2:17]2)=[CH:4][CH2:3]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8063PentanalHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 231420461-[2-(4,4-Dimethylcyclohex-1-enyl)-5-methoxyphenyl]piperazine

Product 1

HCID 231418621-[2-(4,4-Dimethylcyclohex-1-enyl)-5-methoxyphenyl]-4-pentylpiperazineYield 102.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[2-(4,4-dimethylcyclohex-1-enyl)-5-methoxyphenyl]piperazine (90 mg, 0.29 mmol) prepared in Example (1e) in tetrahydrofuran (10 mL) were added valeraldehyde (31 mg, 0.36 mmol), sodium triacetoxyborohydride (95 mg, 0.59 mmol) and acetic acid (35 mg, 0.59 mmol) in that order, and the mixture was stirred for 3 hours. Saturated aqueous sodium hydrogencarbonate was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, the desiccant was filtered off and then the filtrate was concentrated under reduced pressure. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 110 mg of 1-[2-(4,4-dimethylcyclohex-1-enyl)-5-methoxyphenyl]-4-pentylpiperazine as a light yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationthe desiccant was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3af5112db2a047519e77a00c64bfd1a6
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Linked notes

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