Water → HCID 22000239, compound

HRID 1976147Notes

Reaction equation

HRID 1976147 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10]2)[CH:6]=[CH:7][CH:8]=1)#[N:2].C(N(CC)CC)C.O>CS(C)=O>[C:1]([C:3]1[CH:4]=[C:5]([N:9]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10]2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 22000240HCID 22000240, compound

Product 1

HCID 22000239HCID 22000239, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-(3-cyanophenyl)-3-pyrrolidinol (0.65 g, 4.1 mmol) in triethyl amine (5.72 ml, 41 mmol) and DMSO (15 ml) was cooled to 0° C. and pyridine-SO3 (1.96 g, 12.3 mmol) was added. The mixture was stirred at 0° C. for 1 hr and at room temperature for 18 hr. The reaction mixture was poured into water (100 ml) and extracted three times with methylene chloride. The methylene chloride extracts were dried over magnesium sulfate and concentrated in vacuo to give 1-(3-cyanophenyl)-3-pyrrolidinone (0.41 g, 54%) that was used without purification.

Workup

  1. extractionextracted three times with methylene chloride
  2. dry with materialThe methylene chloride extracts were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-abe389567f61407bbfb7b3ebba462d12
Source dataset
uspto-grants-2001_05
Patent number
US06225324B1

Reaction notes

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