Acetic Acid → HCID 19041519, compound

HRID 1683884Notes

Reaction equation

HRID 1683884 reaction equation
C(N(CCC)[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)CC.[OH2:21].Br.[NH+:23]1[CH:28]=C[CH:26]=[CH:25][CH:24]=1.[C:29](O)(=O)[CH3:30]>>[CH2:24]([N:23]([CH:10]1[C:9]2[C:8]3[CH2:16][CH2:17][CH2:5][CH2:6][C:7]=3[CH:15]=[CH:14][C:13]=2[NH:12][C:11]1=[O:21])[CH2:28][CH2:29][CH3:30])[CH2:25][CH3:26]

Participants

5

Reactant 4

HCID 176Acetic Acid2×HCID 962WaterHCID 13342884HCID 13342884, compoundHCID 21226041Pyridinium hydrobromide

Product 1

HCID 19041519HCID 19041519, compoundYield 100%

Conditions

Temperature
80 °C

Procedure

To a solution of dipropyl-(6,7,8,9-tetrahydro-3H-benzo[e]indol-7-yl)amine (200 mg, 0.74 mmol), water (5 ML) in acetic acid (50 mL) was added dropwise to a solution of pyridiniumhydrobromide perbromide (310 mg, 0.91 mmol) in acetic acid (100 mL). The solution was heated and stirred at 80° C. over night. After cooling the solution was evaporated to an aqueous residue, which was basified (10% sodium carbonate) and extracted three times with ethyl acetate. The organic extract was dried (magnesium sulfate), filtered and evaporated to yield 210 mg (100%) of the material.:

Workup

  1. temperatureThe solution was heated
  2. temperatureAfter cooling the solution
  3. customwas evaporated to an aqueous residue, which
  4. extractionextracted three times with ethyl acetate
  5. extractionThe organic extract
  6. dry with materialwas dried (magnesium sulfate)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-6ff20711a00447f88bd67ca7b9297c08
Source dataset
uspto-grants-1997_06
Patent number
US05639778

Reaction notes

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