Pyrrolidine → HCID 11794900, compound

HRID 1860441Notes

Reaction equation

HRID 1860441 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH:9]1[CH2:21][O:22][C:23](OC1C=CC=CC=1)=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH:9]1[CH2:21][O:22][C:23]([N:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1)=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 11373410HCID 11373410, compound

Product 1

HCID 11794900HCID 11794900, compoundYield 50.2%

Procedure

3.12 g (7,5 mmol) of 1,4-dibenzyl-2-phenoxycarbonyloxymethylpiperazine are dissolved in 9.4 ml (15 equivalents; 112.8 mmol) of pyrrolidine in a 100 ml ground-necked conical flask on which is fitted a condenser. The mixture is refluxed in a thermostatically controlled oil bath for 60 hours. After cooling and evaporation of the excess amine, the residue is taken up in CH2Cl2 and washed with water until neutral. After drying the organic phase (MgSO4), filtration on paper and evaporation of the solvent, the product is chromatographed on a column of silica gel, eluting with an MeOH/CH2Cl2 mixture (0.5/99.5 v/v). 1.48 g of 1,4-dibenzyl-2-(1′-pyrrolidinocarbonyloxymethyl)piperazine are thus obtained in the form of a viscous product. Yield 50.2%. Rf=0.38 (5/95 v/v MeOH/CH2Cl2).

Workup

  1. customis fitted a condenser
  2. temperatureThe mixture is refluxed in a thermostatically controlled oil bath for 60 hours
  3. temperatureAfter cooling
  4. customevaporation of the excess amine
  5. washwashed with water until neutral
  6. customAfter drying
  7. filtrationthe organic phase (MgSO4), filtration
  8. customon paper and evaporation of the solvent
  9. customthe product is chromatographed on a column of silica gel
  10. washeluting with an MeOH/CH2Cl2 mixture (0.5/99.5 v/v)

Sources & evidence

ORD record
ord-f347c1d8df7846ebbb0422f076c72803
Source dataset
uspto-grants-2003_03
Patent number
US06531476B1

Reaction notes

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