Dimethylformamide → HCID 14155580, compound

HRID 649194Notes

Reaction equation

HRID 649194 reaction equation
CN(C)[CH:3]=[O:4].O=P(Cl)(Cl)Cl.[CH2:11]([N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])(=O)C.[Na+]>ClCCCl.O>[CH2:11]([N:18]1[C:27]2[C:22](=[CH:23][C:24]([CH:3]=[O:4])=[CH:25][CH:26]=2)[CH2:21][CH2:20][CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 122883501-benzyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 14155580HCID 14155580, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolvent

Procedure

To dimethylformamide (1.7 ml, 0.022 mol) at 0° C. was added dropwise POCl3 (2.0 ml, 0.022 mol) and the mixture allowed to warm and stirred at ambient temperature for 20 minutes, then diluted with 1,2-dichloroethane (5 ml). 1-Benzyl-1,2,3,4-tetrahydroquinoline (4.5 g, 0.020 mol) dissolved in 5 ml of 1,2-dichloroethane was then added and the mixture refluxed 1 hour, then cooled to room temperature. Sodium acetate (9.0g, 0.11 mol), dissolved in the minimum necessary water, was added and the mixture refluxed for 15 minutes. The layers were separated and the aqueous layer extracted 2×10 ml ether.

Workup

  1. temperatureto warm
  2. additionwas then added
  3. temperaturethe mixture refluxed 1 hour
  4. temperaturecooled to room temperature
  5. additionwas added
  6. temperaturethe mixture refluxed for 15 minutes
  7. customThe layers were separated
  8. extractionthe aqueous layer extracted 2×10 ml ether

Sources & evidence

ORD record
ord-09a04662be9d4c38885f2fbd822eb447
Source dataset
uspto-grants-1988_04
Patent number
US04738972

Reaction notes

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