Propanamide, N,N-dimethyl- → HCID 19041550, compound

HRID 1683885Notes

Reaction equation

HRID 1683885 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:33])[CH2:31][CH3:32]>>[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:33])[CH2:31][CH3:32])=[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 12965Propanamide, N,N-dimethyl-HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 13342884HCID 13342884, compound

Product 1

HCID 19041550HCID 19041550, compoundYield 100%

Conditions

Temperature
80 °C

Procedure

A mixture of dipropyl-(6,7,8,9-tetrahydro-3H-benzo[e]indol-7-yl)amine (70 mg, 0.26 mmol) and phosphorous oxychloride (48 μL, 80 mg, 0.52 mmol) in N,N-dimethyl propionamide (250 μL) was heated at 80° C. for 6 hours. After cooling 5M sodium hydroxide was added and the mixture was heated again for 0.5 hour. 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 repetions of the last procedure yielded a residue of 86 mg (100%) of the product.:

Workup

  1. additionwas added
  2. temperaturethe mixture was heated again for 0.5 hour
  3. temperatureAfter cooling
  4. extractionthe mixture was 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-f39181a638a54139a64b5423336aaa9d
Source dataset
uspto-grants-1997_06
Patent number
US05639778

Reaction notes

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