Ethanol → Ethyl 2-(1-benzylpyrrolidin-2-yl)acetate

HRID 1253499Notes

Reaction equation

HRID 1253499 reaction equation
[CH2:1]([OH:3])[CH3:2].S(=O)(=O)(O)O.[CH2:9]([N:16]1[CH2:20][CH2:19][CH2:18][CH:17]1[CH2:21][C:22]#N)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-:25].[Na+].[Na+]>O>[CH2:9]([N:16]1[CH2:20][CH2:19][CH2:18][CH:17]1[CH2:21][C:22]([O:3][CH2:1][CH3:2])=[O:25])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 226628942-(1-Benzylpyrrolidin-2-yl)acetonitrile

Product 1

HCID 11010289Ethyl 2-(1-benzylpyrrolidin-2-yl)acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 3,000 ml roundbottom flask, was placed ethanol (479. g, 10.4 mol), followed by concentrated sulfuric acid (417 g, 4.17 mol). To the mixture was added 2-(1-benzylpyrrolidin-2-yl)acetonitrile (139. g, 695. mmol). The resulting solution was heated to reflux for 4 hours. After cooling to ambient temperature, the solution was diluted with 3,000 ml of water. Adjustment of the pH to 9 was accomplished by the addition of solid sodium carbonate. The resulting solution was extracted three times with 2,000 ml of ethyl acetate and the combined organic layers were concentrated to afford ethyl 2-(1-benzylpyrrolidin-2-yl)acetate, which was used without additional purification.

Workup

  1. customInto a 3,000 ml roundbottom flask, was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for 4 hours
  4. extractionThe resulting solution was extracted three times with 2,000 ml of ethyl acetate
  5. concentrationthe combined organic layers were concentrated

Sources & evidence

ORD record
ord-4db88a77b83d4baf8db3eb6e42c8cd30
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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