HCID 18784149, compound → HCID 18784192, compound

HRID 1108759Notes

Reaction equation

HRID 1108759 reaction equation
C([NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)[CH2:10]1)C1C=CC=CC=1.[ClH:25].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:25].[CH3:24][O:23][C:17]1[CH:16]=[C:15]([CH:11]2[CH2:12][CH2:13][CH2:14][CH:9]([NH2:8])[CH2:10]2)[CH:20]=[CH:19][C:18]=1[O:21][CH3:22]

Participants

4

Reactant 2

HCID 18784149HCID 18784149, compoundHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 18784192HCID 18784192, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-Benzyl-N-[3-(3,4-dimethoxyphenyl)cyclohexyl]amine (3.16 g) was dissolved in ethyl acetate, 4 N HCl-ethyl acetate solution was added, and the mixture was stirred at room temperature for 30 minutes. After concentrating the solvent under reduced pressure, it was dissolved in acetic acid (100 ml), and 10% palladium-carbon (640 mg) was added thereto. After substituting the reaction vessel with hydrogen gas, hydrogen addition was effected for 3 hours at normal pressure, at 80° C. After the reaction, the catalyst was filtered off and the solvent was distilled off under reduced pressure to produce crude crystals which were then washed with diethyl ether to give 2.80 g of 3-(3,4-dimethoxyphenyl)cyclohexylamine hydrochloride (quantitative yield).

Workup

  1. concentrationAfter concentrating the solvent under reduced pressure, it
  2. dissolutionwas dissolved in acetic acid (100 ml)
  3. addition10% palladium-carbon (640 mg) was added
  4. additionwith hydrogen gas, hydrogen addition
  5. waitwas effected for 3 hours at normal pressure, at 80° C
  6. customAfter the reaction
  7. filtrationthe catalyst was filtered off
  8. distillationthe solvent was distilled off under reduced pressure
  9. customto produce crude crystals which
  10. washwere then washed with diethyl ether

Sources & evidence

ORD record
ord-1d5bbbffbe2544ab8687a4c74f8464fb
Source dataset
uspto-grants-2000_05
Patent number
US06069176

Reaction notes

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