Acetic Acid → 1-Cyclopentyl-4-(4-nitrophenyl)piperidine

HRID 1050553Notes

Reaction equation

HRID 1050553 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:16]1(=O)[CH2:20][CH2:19][CH2:18][CH2:17]1.C(O)(=O)C.[BH3-]C#N.[Na+]>CO>[CH:16]1([N:13]2[CH2:12][CH2:11][CH:10]([C:7]3[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[CH2:15][CH2:14]2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 5003444Sodium cyanoborohydrideHCID 159258174-(4-Nitrophenyl)piperidine

Product 1

HCID 1181147581-Cyclopentyl-4-(4-nitrophenyl)piperidineYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(4-Nitrophenyl)piperidine (5 g, 24 mmol) was dissolved in MeOH (240 mL). To the solution were added cyclopentanone (6.5 mL, 73 mmol) and acetic acid (3 mL). The mixture was stirred for 1 hour, and then NaBH3CN (6.1 g, 97 mmol) was added. The mixture was stirred at room temperature for 12 hours. The solvent was removed under reduced pressure, and the residue was suspended in EtOAc. The organic suspension was washed with 1N NaOH (aq), water and brine, dried, concentrated and purified by flash column chromatography (MeOH/DCM) to obtain 1-cyclopentyl-4-(4-nitrophenyl)piperidine (303) (6.5 g, 24 mmol, 100% yield).

Workup

  1. stirringThe mixture was stirred at room temperature for 12 hours
  2. customThe solvent was removed under reduced pressure
  3. washThe organic suspension was washed with 1N NaOH (aq), water and brine
  4. customdried
  5. concentrationconcentrated
  6. custompurified by flash column chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-e9ddcd0259024c1883835d9366ae0ad8
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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