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

HRID 1637266Notes

Reaction equation

HRID 1637266 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.N1C=CC=CC=1.[C:26](OC(=O)C)(=[O:28])[CH3:27].O>C(Cl)Cl>[C:26]([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:28])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 101988185-Amino-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole

Product 1

HCID 193481405-(N-acetylamino)-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indoleYield 61.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A portion (70 mg) of the compound obtained in Example 81 was dissolved in anhydrous methylene chloride (10 ml) and to the solution were added pyridine (22 mg) and acetic anhydride (29 mg). The mixture was stirred for 20 minutes at room temperature. To the reaction mixture was added water, followed by extraction with methylene chloride. The organic layer was washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=1:2-1:1-2:1) to yield 50 mg (61%) of the titled compound as a pale brown powder.

Workup

  1. extractionfollowed by extraction with methylene chloride
  2. washThe organic layer was washed with 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
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1:2-1:1-2:1)

Sources & evidence

ORD record
ord-35c101d5344642c7af2f242cd0899cbd
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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