rac-(1R,2R)-2-phenylcyclopentan-1-amine hydrochloride → cis-2-Cyclohexylcyclopentylamine hydrochloride

HRID 1704238Notes

Reaction equation

HRID 1704238 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 70050481cis-2-Cyclohexylcyclopentylamine hydrochlorideYield 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-811b11ae171a4528b2eec10af0c3cc7a
Source dataset
uspto-grants-1978_11
Patent number
US04126613

Reaction notes

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