Potassium Carbonate → 1-Pyrrolidinepropanol

HRID 454210Notes

Reaction equation

HRID 454210 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:7][CH2:8][CH2:9][OH:10].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:10][CH2:9][CH2:8][CH2:7][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123133-Chloro-1-propanolHCID 31268Pyrrolidine

Product 1

HCID 2093421-PyrrolidinepropanolYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of pyrrolidine (50 g, 0.7 mol) and 3-chloropropan-1-ol (66.15 g, 0.7 mol) in acetonitrile (1l) containing potassium carbonate (145 g, 1.05 mol) was refluxed for 20 hours. After cooling, the mixture was filtered, the solid was washed with acetonitrile and the filtrate was evaporated. The residue was distilled at about 130° C. under about 70 mmHg to give 1-(3-hydroxypropyl)pyrrolidine (62.1 g, 69%).

Workup

  1. temperaturewas refluxed for 20 hours
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. washthe solid was washed with acetonitrile
  5. customthe filtrate was evaporated
  6. distillationThe residue was distilled at about 130° C. under about 70 mmHg

Sources & evidence

ORD record
ord-d66dfa54de9b48409b90f617c7b96a18
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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