HCID 18784188, compound → HCID 69973134, compound

HRID 1108770Notes

Reaction equation

HRID 1108770 reaction equation
[ClH:1].C([NH:9][CH2:10][CH:11]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:12]1)C1C=CC=CC=1.[H][H]>C(O)(=O)C.[C].[Pd]>[ClH:1].[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([CH:13]2[CH2:14][CH2:15][CH:11]([CH2:10][NH2:9])[CH2:12]2)=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 18784188HCID 18784188, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 69973134HCID 69973134, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

N-Benzyl-N-[3-(4-methoxyphenyl)cyclopentylmethyl]amine hydrochloride (6.30 g) was dissolved in acetic acid (130 ml), and 10% palladium-carbon (1.1 g) was added. After substituting the reaction vessel with hydrogen gas, hydrogen addition was carried out at normal pressure, 80° C. for 2 hours. After the reaction, the catalyst was filtered off and the solvent was distilled off under reduced pressure to produce light yellow crystals which were then washed with diethyl ether to give 4.31 g of 3-(4-methoxyphenyl) cyclopentylmethylamine hydrochloride (94.0%).

Workup

  1. customAfter the reaction
  2. filtrationthe catalyst was filtered off
  3. distillationthe solvent was distilled off under reduced pressure
  4. customto produce light yellow crystals which
  5. washwere then washed with diethyl ether

Sources & evidence

ORD record
ord-f6485d7a50794c76943ba7e2ab3094b4
Source dataset
uspto-grants-2000_05
Patent number
US06069176

Reaction notes

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