Benzene → 4-(3,6-Dihydro-4-(1-pyrrolidinyl)-1(2H)-pyridinyl]benzonitrile

HRID 1199637Notes

Reaction equation

HRID 1199637 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[NH:16]1[CH2:20][CH2:19][CH2:18][C:17]1=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O>[N:16]1([C:2]2[CH2:7][CH2:6][N:5]([C:8]3[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=3)[CH2:4][CH:3]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 120252-PyrrolidoneHCID 110198874-(4-Oxopiperidin-1-yl)benzonitrile

Product 1

HCID 146267924-(3,6-Dihydro-4-(1-pyrrolidinyl)-1(2H)-pyridinyl]benzonitrileYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 24 g (0.1199 mol) of the compound of (b), 15 ml (12.78 g/0.1796 mol) of pyrrolidone, 240 mg of p-toluenesulfonic acid, and 100 ml of benzene is stirred at reflux with the azeotropic removal of water for 6 hours. After cooling, the resulting precipitate is collected and triturated with ethyl ether to afford 20 g (66%) of title compound: m.p. 126°-129° C.; IR (KBr) 2200, 1635, and 1600 cm-1 ; 'H NMR (CDCl3) δ 7.48 (d, 2H), 6.7 (d, 2H), 4.3-4.1 (m, 1H), 3.95-3.45 (m, 4H), 3.2-2.85 (m, 4H), 2.65-2.25 (m, 2H), and 1.95-1.75 (m, 4H).

Workup

  1. temperatureAfter cooling
  2. customthe resulting precipitate is collected
  3. customtriturated with ethyl ether

Sources & evidence

ORD record
ord-dd272fcdd8fd47379893fa4f28c29894
Source dataset
uspto-grants-1990_02
Patent number
US04902685

Reaction notes

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