Dimethylformamide → HCID 19041549, compound

HRID 1683878Notes

Reaction equation

HRID 1683878 reaction equation
[CH2:1]([N:4]([CH2:18][CH2:19][CH3:20])[CH:5]1[CH2:17][C:9]2=[CH:10][CH:11]=[C:12]3[C:16]([NH:15][CH:14]=[CH:13]3)=[C:8]2[CH2:7][CH2:6]1)[CH2:2][CH3:3].P(Cl)(Cl)(Cl)=O.CN(C)[CH:28]=[O:29]>>[CH2:18]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:17][C:9]2=[CH:10][CH:11]=[C:12]3[C:16]([NH:15][CH:14]=[C:13]3[CH:28]=[O:29])=[C:8]2[CH2:7][CH2:6]1)[CH2:19][CH3:20]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 391101HCID 391101, compound

Product 1

HCID 19041549HCID 19041549, compoundYield 82%

Conditions

Temperature
50 °C

Procedure

A solution of di-n-propyl-(6,7,8,9-tetrahydro-1H-benzo[g]indol-7yl)amine, (3a, Chart 1)(0.90 g, 3.33 mmol) in dimethyl formamide (10 mL) was added dropwise to an ice-cooled solution of phosphorous oxychloride (1.2 ml, 0.73 g, 4.8 mmol) under an inert atmosphere. The solution was stirred for 10 minutes and was then heated to 50° C. After stirring for 3 hours, the solution was allowed to reach ambient temperature, stirred overnight and was then poured on ice. After basification, the mixture was heated to 80° C. for 10 minutes and then cooled. Extraction three times (dichloromethane), followed by drying (magnesium sulfate), filtering and evaporation several times with 99% ethanol, yielded 0.82 g (82%) of the material. This material was further purified on a silica column (dichloromethane/methanol, 3:1) to yield 0.53 g (53%) of the pure material as an oil.

Workup

  1. stirringAfter stirring for 3 hours
  2. customto reach ambient temperature
  3. stirringstirred overnight
  4. additionwas then poured on ice
  5. temperatureAfter basification, the mixture was heated to 80° C. for 10 minutes
  6. temperaturecooled
  7. extractionExtraction three times (dichloromethane)
  8. dry with materialby drying (magnesium sulfate)
  9. filtrationfiltering
  10. customevaporation several times with 99% ethanol

Sources & evidence

ORD record
ord-8f9db080c44e4087a9a6ea6ca11b4305
Source dataset
uspto-grants-1997_06
Patent number
US05639778

Reaction notes

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