Water → 5-(N-benzoylamino)-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole

HRID 1637267Notes

Reaction equation

HRID 1637267 reaction equation
[NH2:1][CH:2]1[C:12]2[C:13]3[C:5](=[C:6]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[NH:7][C:8]=3[CH:9]=[CH:10][CH:11]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>C(Cl)Cl>[C:27]([NH:1][CH:2]1[C:12]2[C:13]3[C:5](=[C:6]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[NH:7][C:8]=3[CH:9]=[CH:10][CH:11]=2)[CH2:4][CH2:3]1)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 101988185-Amino-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole

Product 1

HCID 193482265-(N-benzoylamino)-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indoleYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A portion (70 mg) of the compound obtained in Example 81 was dissolved in anhydrous methylene chloride (15 ml) and to the solution were added triethylamine (69 μl) and benzoyl chloride (29 μl). The mixture was stirred for 1 hour at room temperature. To the reaction mixture was added water, followed by extraction with methylene chloride. The organic layer was washed with 1N aqueous solution of sodium hydroxide, water and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure to yield 90 mg (91%) of the titled compound.

Workup

  1. extractionfollowed by extraction with methylene chloride
  2. washThe organic layer was washed with 1N aqueous solution of sodium hydroxide, water and saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e9305ab8d6404cc09a9368e43911d086
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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