rac-(1R,2R)-2-phenylcyclopentan-1-amine hydrochloride → HCID 70050481, compound

HRID 261996

Reaction equation

HRID 261996 reaction equation
[ClH:1].[C:2]1([C@H:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[NH2:13])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>O>[ClH:1].[CH:2]1([C@H:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[NH2:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 70051154rac-(1R,2R)-2-phenylcyclopentan-1-amine hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 70050481HCID 70050481, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using rhodium-on-charcoal catalyst in a Paar shaker, 12.6 g of cis-2-phenylcyclopentylamine hydrochloride, M.P. 204°-206° C. in 100 ml of water was hydrogenated. In 20 hours when the theoretical amount of hydrogen had been taken up the catalyst was removed by filtration, the filtrate made basic with sodium hydroxide solution, and the resulting precipitate was extracted into ether. After evaporation of the ether the residue was distilled, B.P. 100°-102° C. (6.0 mm). The hydrochloride salt was prepared and recrystallized from isopropanolether to give 4.4 g of cis-2-(cyclohexyl)cyclopentylamine hydrochloride, M.P. 174°-176° C.

Workup

  1. customthe catalyst was removed by filtration
  2. extractionthe resulting precipitate was extracted into ether
  3. customAfter evaporation of the ether the residue
  4. distillationwas distilled
  5. customrecrystallized from isopropanolether

Sources & evidence

ORD record
ord-4faf5b9c58494fa0b2cabdeda263308e
Source dataset
uspto-grants-1979_05
Patent number
US04153235

Linked notes

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