Hydrogen chloride-ethyl acetate → HCID 69971262, compound

HRID 1108751Notes

Reaction equation

HRID 1108751 reaction equation
C([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][C@H:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[CH2:10]1)C1C=CC=CC=1.[ClH:23].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:23].[CH3:22][O:21][C:17]1[CH:16]=[C:15]([C@H:11]2[CH2:12][CH2:13][CH2:14][C@H:9]([NH2:8])[CH2:10]2)[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 69972431HCID 69972431, compound

Product 1

HCID 69971262HCID 69971262, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(trans)-N-Benzyl-N-[3-(3-methoxyphenyl)cyclohexyl]amine (6.59 g) was dissolved in ethyl acetate (20 ml), and then 4 N HCl-ethyl acetate solution (20 ml) was added while cooling on ice, and the mixture was stirred at room temperature for 30 minutes. After concentrating the reaction solution under reduced pressure, 10% palladium-carbon (1.3 g) and acetic acid (60 ml) were added for hydrogen addition at an external temperature of 80° C. for 8 hours. After filtering off the solvent from the reaction solution, the solvent was concentrated under reduced pressure (repeated azeotropy with ethanol and toluene) to give 5.40 g of (trans)-3-(3-methoxyphenyl)cyclohexylamine hydrochloride (quantitative yield).

Workup

  1. temperaturewhile cooling on ice
  2. concentrationAfter concentrating the reaction solution under reduced pressure, 10% palladium-carbon (1.3 g) and acetic acid (60 ml)
  3. additionwere added for hydrogen addition at an external temperature of 80° C. for 8 hours
  4. filtrationAfter filtering off the solvent from the reaction solution
  5. concentrationthe solvent was concentrated under reduced pressure (

Sources & evidence

ORD record
ord-caa9e9d325ad49b3b54c2dc71f5d4e50
Source dataset
uspto-grants-2000_05
Patent number
US06069176

Reaction notes

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