Hydrochloric Acid → 3-Cyclopentylaniline hydrochloride

HRID 733198Notes

Reaction equation

HRID 733198 reaction equation
C([N:8](CC1C=CC=CC=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:10]=1)C1C=CC=CC=1.COC(O)C.C(Cl)[Cl:33].Cl>CO.[OH-].[OH-].[Pd+2]>[ClH:33].[CH:15]1([C:11]2[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=2)[NH2:8])[CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 30156371-MethoxyethanolHCID 69047054N,N-dibenzyl-3-cyclopentyl-aniline

Product 1

HCID 690470023-Cyclopentylaniline hydrochloride

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

N,N-Dibenzyl-3-cyclopentyl-aniline (6.07 g, 17.03 mmol) was hydrogenated over Pd(OH)2 (600 mg) under 10 bars in a mixture of MeOH (80 ml), methoxyethanol (20 ml), CH2Cl2 (20 ml) and concentrated HCl (1.63 ml) for 20 h, The catalyst was removed by filtration and the solvent was removed under reduced pressure. The residue was partitioned between CH2Cl2 and water. The pH was set to about 10 by adding NaOH in pellets. The organic layer was washed with brine, dried over MgSO4 and concentrated under reduced pressure to give 2.65 g of the expected aniline. The hydrochloride was obtained by treatment with ethereal HCl: 2.38 g, yield: 71%. HPLC: 100%.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was partitioned between CH2Cl2 and water
  4. additionby adding NaOH in pellets
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-39576a907428484eb43ad3fdf39885ee
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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