1,2,3,6-Tetrahydro-4-phenylpyridine → HCID 53925922, compound

HRID 1263151Notes

Reaction equation

HRID 1263151 reaction equation
O[CH:2]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]2)[CH2:3][CH2:4]Cl.[C:17]1([C:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH:24]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[C:17]1([C:23]2[CH2:28][CH2:27][N:26]([CH2:4][CH:3]=[CH:2][C:6]3[CH:7]=[C:8]4[C:13](=[CH:14][CH:15]=3)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]4)[CH2:25][CH:24]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 825531,2,3,6-Tetrahydro-4-phenylpyridineHCID 516892Sodium BicarbonateHCID 202294596-(1-Hydroxy-3-chloropropyl)-3,4-dihydrocarbostyril

Product 1

HCID 53925922HCID 53925922, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.5 Grams of 6-[1-hydroxy-3-chloropropyl]-3,4-dihydrocarbostyril and 3.0 g of 4-phenyl-1,2,5,6-tetrahydropyridine were mixed in 50 ml of toluene and the mixture was refluxed by heating for 5 hours, then toluene was removed by distillation. To the residue thus obtained was added 50 ml of 5%-sodium hydrogencarbonate aqueous solution and was extracted with chloroform. The chloroform layer was washed with water and dried, then chloroform was removed by distillation. The residue thus obtained was recrystallized from ethanol to obtain 2.1 of 6-[3-(4-phenyl-1,2,5,6-tetrahydropyridyl)-1-propenyl]-3,4-dihydrocarbostyril in light yellow plate-like crystals. Melting point: 182°-183° C. (decomposed).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureby heating for 5 hours
  3. customtoluene was removed by distillation
  4. customTo the residue thus obtained
  5. extractionwas extracted with chloroform
  6. washThe chloroform layer was washed with water
  7. customdried
  8. customchloroform was removed by distillation
  9. customThe residue thus obtained
  10. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-1ca000429a964c1c95d5c8f834764e2b
Source dataset
uspto-grants-1984_06
Patent number
US04455422

Reaction notes

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