Sodium Iodide → (3R)-1-(1-benzyl-pyrrolidin-3-yl)-piperidine

HRID 478932Notes

Reaction equation

HRID 478932 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([NH2:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCO[CH2:18][CH2:19]Cl.[C:21]([O-])([O-])=O.[K+].[K+].[Na+].[I-].[CH3:29][C:30]#N>>[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([N:13]2[CH2:19][CH2:18][CH2:29][CH2:30][CH2:21]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 8115Bis(2-chloroethyl) etherHCID 11430Potassium CarbonateHCID 1519354(3R)-1-benzylpyrrolidin-3-amine

Product 1

HCID 69830750(3R)-1-(1-benzyl-pyrrolidin-3-yl)-piperidine

Procedure

The mixture of (3R)-(−)-1-benzyl-pyrrolidin-3-ylamine (10 mmol, 1.76 g), bis(2-chloroethyl)ether (11 mmol, 1.29 mL), K2CO3 (40 mmol, 5.52 g) and NaI (0.4 mmol, 60 mg) in CH3CN (100 mL) was heated at reflux for 36 h under N2. It was then absorbed on silica gel (10 g) and evaporated to dryness. The solid was loaded on silica gel column and subjected to flash chromatograph (CH2Cl2/CH3OH=60/1-20/1). (3R)-1-(1-benzyl-pyrrolidin-3-yl)-piperidine 7 was obtained as white gum (1.4 g, 60%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 36 h under N2
  3. customIt was then absorbed on silica gel (10 g)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-b07c84b1ce40424fb0efdb0110ba10ec
Source dataset
uspto-grants-2003_11
Patent number
US06642232B2

Reaction notes

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