Hydrochloric Acid → 4-(1-Cyclopentylpiperidin-4-yl)aniline hydrochloride

HRID 1050554Notes

Reaction equation

HRID 1050554 reaction equation
[CH:1]1([N:6]2[CH2:11][CH2:10][CH:9]([C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=3)[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H].[ClH:23]>CC(O)C.[Pd]>[ClH:23].[CH:1]1([N:6]2[CH2:11][CH2:10][CH:9]([C:12]3[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=3)[CH2:8][CH2:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 1181147581-Cyclopentyl-4-(4-nitrophenyl)piperidineHCID 178418361HCID 178418361, compound

Product 1

HCID 1181146604-(1-Cyclopentylpiperidin-4-yl)aniline hydrochlorideYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

1-Cyclopentyl-4-(4-nitrophenyl)piperidine (303) (6.5 g, 24 mmol) was dissolved in IPA (70 mL) and 2M HCl (aq) (18 mL), and 10% Pd/C (2 g) was added. The resulting mixture was agitated on Parr shaker under 50 psi hydrogen for 18 hours. The reaction mixture was filtered through celite, and the solvent was removed under reduced pressure to give 4-(1-cyclopentylpiperidin-4-yl)aniline hydrochloride (304) (4.0 g, 14 mmol, 60% yield).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-80bb468f16184f54bab786b28aa2a70c
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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