Hydrochloric Acid → 1-[3-Piperazin-1-yl-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]ethanone

HRID 32208Notes

Reaction equation

HRID 32208 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([C:20](=[O:22])[CH3:21])[CH:17]=[CH:16][C:15]=2[CH:23]2[CH2:28][C:27]([CH3:30])([CH3:29])[CH2:26][C:25]([CH3:32])([CH3:31])[CH2:24]2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>C(OCC)C.CCCCCCC>[N:11]1([C:14]2[CH:19]=[C:18]([C:20](=[O:22])[CH3:21])[CH:17]=[CH:16][C:15]=2[CH:23]2[CH2:24][C:25]([CH3:31])([CH3:32])[CH2:26][C:27]([CH3:30])([CH3:29])[CH2:28]2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 597694454-[5-Acetyl-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine-1-carboxylic acid t-butyl ester

Product 1

HCID 231416551-[3-Piperazin-1-yl-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]ethanoneYield 46%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8900HeptaneSolvent

Procedure

A mixture of 4-[5-acetyl-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine-1-carboxylic acid t-butyl ester (163 mg, 0.368 mmol) produced in Example (82a), diethyl ether (2 mL) and heptane (2 mL) was stirred at room temperature. A 4N solution of hydrogen chloride in ethyl acetate (2 mL, 8 mmol) was added thereto, and the mixture was stirred for 18 hours and 30 minutes. Saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture and extraction was performed with diethyl ether. The separated organic layer was washed with water and brine in that order. The mixture was then filtered through Celite, and the filtrate was concentrated under reduced pressure. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 58 mg of the title compound as a light yellow oil.

Workup

  1. stirringthe mixture was stirred for 18 hours and 30 minutes
  2. washThe separated organic layer was washed with water and brine in that order
  3. filtrationThe mixture was then filtered through Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-df17c04070f44d9280ef6685e5c78d22
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Reaction notes

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