Dimethylformamide → HCID 19041563, compound

HRID 1683887Notes

Reaction equation

HRID 1683887 reaction equation
[Br:1][C:2]1[C:3]2[CH2:14][CH2:13][CH:12]([N:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])[CH2:11][C:4]=2[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.P(Cl)(Cl)(Cl)=O.[OH-].[Na+].CN(C)[CH:31]=[O:32]>O>[Br:1][C:2]1[C:3]2[CH2:14][CH2:13][CH:12]([N:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])[CH2:11][C:4]=2[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH:31]=[O:32]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 19041542HCID 19041542, compound

Product 1

HCID 19041563HCID 19041563, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of (9-Bromo-5,6,7,8-tetrahydro-1H-benzo[f]indol-6-yl)-dipropyl amine (50 mg, 0.14 mmol) in N,N-dimethyl formamide (3 mL) was cooled to 0° C. To this solution was added a cooled solution of phosphorus oxychloride (26 μL, 0.28 mmol) in N,N-dimethyl formamide (1 mL), which had been prepared 20 minutes previous to use. The mixture was stirred at ambient temperature for 30 minutes and then for 30 minutes at 50° C. an additional 30 minutes. The reaction mixture was then treated with a 1M sodium hydroxide solution (5 mL) with heating and stirring maintained for an additional hour. After cooling, the solution was diluted with water (25 mL) and extracted with several portions of diethyl ether. The combined etheral extracts were washed with water, brine, dried over magnesium sulfate, and the solvent evaporated. The residue was chromatographed on a silica column, using methanol as the eluant. This was then repeated with diethyl ether as eluant. The yield of the pure title compound was 50 mg (95%).:

Workup

  1. customhad been prepared 20 minutes previous
  2. waitfor 30 minutes at 50° C. an additional 30 minutes
  3. temperaturewith heating
  4. stirringstirring
  5. temperaturemaintained for an additional hour
  6. temperatureAfter cooling
  7. extractionextracted with several portions of diethyl ether
  8. washThe combined etheral extracts were washed with water, brine
  9. dry with materialdried over magnesium sulfate
  10. customthe solvent evaporated
  11. customThe residue was chromatographed on a silica column

Sources & evidence

ORD record
ord-038b43d76f8a4d1e8e62d9488bc99dc2
Source dataset
uspto-grants-1997_06
Patent number
US05639778

Reaction notes

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