Benzene → 1-(3,6-Dihydro-2H-thiopyran-4-yl)pyrrolidine

HRID 1730069Notes

Reaction equation

HRID 1730069 reaction equation
[S:1]1[CH2:6][CH2:5][C:4](=O)[CH2:3][CH2:2]1.[NH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.C1C=CC=CC=1>O>[N:8]1([C:4]2[CH2:5][CH2:6][S:1][CH2:2][CH:3]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 241BenzeneHCID 31268PyrrolidineHCID 66173Tetrahydrothiopyran-4-one

Product 1

HCID 132874681-(3,6-Dihydro-2H-thiopyran-4-yl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 103 g (0.89 mole) of tetrahydrothiopyran-4-one, 95 g (1.33 moles) of pyrrolidine, and one l. of anhydrous benzene is heated under reflux in a nitrogen atmosphere for 2 hours until the theoretical amount of water has collected in a Dean-Stark trap. The solvent is distilled, and the residue is fractionated under reduced pressure to provide 5,6-dihydro-4-(1-pyrrolidinyl)-2H-thiopyran as a colorless liquid, b.p. 124° (0.01 mm).

Workup

  1. customhas collected in a Dean-Stark trap
  2. distillationThe solvent is distilled

Sources & evidence

ORD record
ord-c451294acae343c1a14cd31e48749de5
Source dataset
uspto-grants-1976_11
Patent number
US03991076

Reaction notes

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