Piperidine → N-(N-benzylpyrrolidin-3-yl)piperidine

HRID 1916638Notes

Reaction equation

HRID 1916638 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[CH2:21]([N:28]1[CH2:32][CH2:31][CH2:30][C:29]1=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])(O)=O.[Na+]>C1COCC1.C(O)(=O)C>[CH2:21]([N:28]1[CH2:32][CH2:31][CH:30]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 791761-Benzyl-3-pyrrolidoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18002297N-(N-benzylpyrrolidin-3-yl)piperidine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

12.7 g (60.0 mmol) NaBH(OAc)3 and 2.3 mL acetic acid are added to a solution of 4.94 mL (50.0 mmol) piperidine and 8.03 mL (50.0 mmol) N-benzylpyrrolidinone in 200 mL THF. The reaction is stirred overnight at RT. The reaction solution is combined with 200 mL saturated NaHCO3 solution and extracted twice with 200 mL EtOAc. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac. The purification is carried out by column chromatography on silica gel (EtOAc/MeOH/NH3 8:2:0.2).

Workup

  1. extractionextracted twice with 200 mL EtOAc
  2. dry with materialThe organic phase is dried over MgSO4
  3. customThe purification

Sources & evidence

ORD record
ord-31afed56ce754ebda86baee466e6178a
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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