Pyrrolidine → HCID 54227605, compound

HRID 864810Notes

Reaction equation

HRID 864810 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]=O.[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1>C(O)C>[N:10]1([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[CH:8]=[C:12]2[CH2:13][CH2:14][N:10]=[CH:11]2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 140466744-Chloropyridine-3-carbaldehyde

Product 1

HCID 54227605HCID 54227605, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-chloropyridine-3-carboxaldehyde (10 g, prepared according to the method described in J. Het. Chem, 25, 81), pyrrolidine (25 ml) and ethanol (100 ml) was heated under reflux for 5 hours, then concentrated. The residue was purified by flash column chromatography (grade II alumina) eluting first with dichloromethane and then with methanol/dichloromethane (1:200) to give 3-[[4-(pyrrolidin-1-yl)pyridin-3-yl]methylidene]-1-pyrroline (900 mg) as a white solid. NMR (d6DMSO): δ1.8(4H,m); 2.5(2H,m); 3.3(4H,m); 3.95(2H,m); 6.6(1H,d); 7.0(1H,t), 7.9(1H,t), 8.0(1H,d); 8.15(1H,s); m/e 228(M+H)+ ; calculated for C14H17N3 : C, 74.0; H, 7.5; N, 18.5; found C, 74.1; H, 7.7; N, 18.4%.

Workup

  1. customprepared
  2. temperatureunder reflux for 5 hours
  3. concentrationconcentrated
  4. customThe residue was purified by flash column chromatography (grade II alumina)
  5. washeluting first with dichloromethane

Sources & evidence

ORD record
ord-deb840ddd9ac4e29923c2a01a10efa4b
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

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