Pyrrolidine → HCID 21530393, compound

HRID 1657812Notes

Reaction equation

HRID 1657812 reaction equation
[S:1]1(=[O:14])(=[O:13])[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5](=O)[CH2:4][CH2:3][CH2:2]1.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[N:15]1([C:5]2[C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[S:1](=[O:14])(=[O:13])[CH2:2][CH2:3][CH:4]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 774902HCID 774902, compound

Product 1

HCID 21530393HCID 21530393, compoundYield 102.5%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

A solution of 20.6 g (0.1 mol) of 3,4-dihydro-1-benzothiepin-5(2H)-one 1,1-dioxide, 9.6 g of pyrrolidine and 250 mg of p-toluenesulfonic acid in 250 ml of benzene was refluxed under a nitrogen atmosphere for 20 hours, using a Dean-Stark apparatus to remove the water which formed. Removal of the solvent under reduced pressure gave 27 g of a viscous oil which was used without further purification. The infrared spectrum showed the absence of a ketone band and the presence of a strong enamine band at 1620 cm-1.

Workup

  1. customto remove the water which
  2. customformed
  3. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-4922c69a931c4715948c2a8510de1140
Source dataset
uspto-grants-1976_06
Patent number
US03962261

Reaction notes

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