Benzene → 1,2,3,6-Tetrahydro-1-[4-(methylsulfonyl)phenyl]-4-(1-pyrrolidinyl)pyridine

HRID 1199638Notes

Reaction equation

HRID 1199638 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[NH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH:15]=[C:14]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 31268PyrrolidineHCID 141563991-(4-Methanesulfonylphenyl)piperidin-4-one

Product 1

HCID 146267951,2,3,6-Tetrahydro-1-[4-(methylsulfonyl)phenyl]-4-(1-pyrrolidinyl)pyridineYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 24 g (0.0947 mol) of the compound of (b), 12 ml (10.2 g/0.143 mol) of pyrrolidine, 240 mg of p-toluenesulfonic acid and 150 ml of benzene is heated at reflux with the azeotropic removel of water for 6 hours. After cooling the resulting precipitate is collected and triturated with ethyl ether to afford 22.5 g (78%) of title compound: m.p. 141°-143° C.; IR (KBr) 1650, 1580, 1300, and 1130 cm-1 ; NMR (CDCl3)δ 7.75 (d, 2H), 6.85 (d, 2H), 4.30-4.10 (m, 1H), 3.95-3.45 (m, 4H), 3.25-2.85 (m, 4H) 3.05 (s, 3H), 2.65-2.30 (m, 2H), and 1.95-1.70 (m, 4H).

Workup

  1. temperatureAfter cooling the resulting precipitate
  2. customis collected
  3. customtriturated with ethyl ether

Sources & evidence

ORD record
ord-63b058cfce684309b629a5fb7f2f01bb
Source dataset
uspto-grants-1990_02
Patent number
US04902685

Reaction notes

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