Methanol → 2a-[4-{4-(2-Hydroxyphenyl)piperazinyl}butyl]-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

HRID 276896Notes

Reaction equation

HRID 276896 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]23[CH2:30][CH2:29][CH2:28][C:26]4[C:27]2=[C:22]([CH:23]=[CH:24][CH:25]=4)[NH:21][C:20]3=[O:31])[CH2:11][CH2:10]1.B(Br)(Br)Br.CO.C(OCC)(=O)C>C1C=CC=CC=1>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]23[CH2:30][CH2:29][CH2:28][C:26]4[C:27]2=[C:22]([CH:23]=[CH:24][CH:25]=4)[NH:21][C:20]3=[O:31])[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 98450062a-[4-{4-(2-Methoxyphenyl)piperazinyl}butyl]-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

Product 1

HCID 155426302a-[4-{4-(2-Hydroxyphenyl)piperazinyl}butyl]-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-oneYield 59%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2a-[4-{4-(2-Methoxyphenyl)piperazinyl}butyl]-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H) -one (100 mg, 0.24 mmol) was dissolved in benzene (2 ml) to which was subsequently added dropwise boron tribromide (240 mg, 0.96 mmol), and the resulting mixture was stirred at room temperature for 2 hours and then at 60° C. for 24 hours. The reaction solution was mixed with methanol and ethyl acetate, washed with water and saturated brine and dried with anhydrous sodium sulfate. Then the solvent was evaporated under a reduced pressure to obtain 57 mg of the title compound (0.14 mmol, 59% in yield).

Workup

  1. waitat 60° C. for 24 hours
  2. washwashed with water and saturated brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. customThen the solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-19ec57bb4b1f478495328ec37bf99be4
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Reaction notes

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