Acetic Acid → 2a-[4-(4-Acetyl-4-phenyl-piperidyl)butyl]-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

HRID 276910Notes

Reaction equation

HRID 276910 reaction equation
[CH:1]([CH2:3][CH2:4][CH2:5][C:6]12[CH2:17][CH2:16][CH2:15][C:13]3[C:14]1=[C:9]([CH:10]=[CH:11][CH:12]=3)[NH:8][C:7]2=[O:18])=O.Cl.[C:20]([C:23]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)(=[O:22])[CH3:21].C(O)(=O)C.C(OCC)(=O)C>ClCCCl>[C:20]([C:23]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:24][CH2:25][N:26]([CH2:1][CH2:3][CH2:4][CH2:5][C:6]23[CH2:17][CH2:16][CH2:15][C:13]4[C:14]2=[C:9]([CH:10]=[CH:11][CH:12]=4)[NH:8][C:7]3=[O:18])[CH2:27][CH2:28]1)(=[O:22])[CH3:21]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 27237674-Acetyl-4-phenylpiperidine hydrochlorideHCID 155426362a-(3-Formylpropyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one

Product 1

HCID 108952842a-[4-(4-Acetyl-4-phenyl-piperidyl)butyl]-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-oneYield 24%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2a-(3-Formylpropyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one (180 mg, 0.72 mmol), 4-acetyl-4-phenylpiperidine hydrochloride (190 mg, 0.79 mmol), acetic acid (430 mg, 7.2 mmol) and sodium triacetoxyborate (310 mg, 1.4 mmol) were stirred in 1,2-dichloroethane (3 ml) at a room temperature for 20 hours. The reaction solution was mixed with ethyl acetate (80 ml), washed with sodium hydroxide aqueous solution (1 N) and saturated brine and dried with anhydrous sodium sulfate. Then the compound obtained by the evaporation of the solvent under a reduced pressure was separated and purified by a silica gel column chromatography to obtain 74 mg of the title compound (0.17 mmol, 24% in yield).

Workup

  1. washwashed with sodium hydroxide aqueous solution (1 N) and saturated brine
  2. dry with materialdried with anhydrous sodium sulfate
  3. customThen the compound obtained by the evaporation of the solvent under a reduced pressure
  4. customwas separated
  5. custompurified by a silica gel column chromatography

Sources & evidence

ORD record
ord-5c5af0bee83b465ca2c0c8a905dc35bc
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Reaction notes

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