Sodium Hydroxide → HCID 19041535, compound

HRID 1683886Notes

Reaction equation

HRID 1683886 reaction equation
[CH2:1]([N:4]([CH2:18][CH2:19][CH3:20])[CH:5]1[CH2:17][CH2:16][C:8]2[C:9]3[CH:10]=[CH:11][NH:12][C:13]=3[CH:14]=[CH:15][C:7]=2[CH2:6]1)[CH2:2][CH3:3].P(Cl)(Cl)(Cl)=O.[OH-].[Na+].CN(C)[C:30](=[O:32])[CH3:31]>>[CH2:18]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:17][CH2:16][C:8]2[C:9]3[C:10]([C:30](=[O:32])[CH3:31])=[CH:11][NH:12][C:13]=3[CH:14]=[CH:15][C:7]=2[CH2:6]1)[CH2:19][CH3:20]

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 31374DimethylacetamideHCID 13342884HCID 13342884, compound

Product 1

HCID 19041535HCID 19041535, compoundYield 89%

Conditions

Temperature
80 °C

Procedure

A mixture of dipropyl-(6,7,8,9-tetrahydro-3H-benzo[e]indol-7-yl)amine (55 mg, 0.20 mmol) and phosphorous oxychloride (130 μL, 213 mg, 1.39 mmol) in N,N-dimethylacetamide (200 μL) was heated at 80° C. for 4 hours. After cooling 5M sodium hydroxide was added and the mixture was heated again for 0.5 hours. After cooling the mixture was extracted 3 times with ethyl acetate, dried (magnesium sulfate), filtered and evaporated to yield a residue to which 99% ethanol was added. This was then evaporated to dryness. A few repetitions of the last procedure yielded a residue of 56 mg (89%) of the product, which was further purified on silica using methanol as eluant to give the pure material as a solid.:

Workup

  1. additionwas added
  2. temperaturethe mixture was heated again for 0.5 hours
  3. temperatureAfter cooling the mixture
  4. extractionwas extracted 3 times with ethyl acetate
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated
  8. customto yield a residue to which 99% ethanol
  9. additionwas added
  10. customThis was then evaporated to dryness

Sources & evidence

ORD record
ord-53a4bd77a9284749bfc840a3f5ec4a74
Source dataset
uspto-grants-1997_06
Patent number
US05639778

Reaction notes

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