Acetic Acid → 2a-(4-(4-(1-Indanyl)-piperazin-1-yl)butyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one

HRID 2301136Notes

Reaction equation

HRID 2301136 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.[CH:20]1([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(OCC)(=O)C>[CH:20]1([N:29]2[CH2:34][CH2:33][N:32]([CH2:1][CH2:3][CH2:4][CH2:5][C:6]34[CH2:17][CH2:16][CH2:15][C:13]5[C:14]3=[C:9]([CH:10]=[CH:11][CH:12]=5)[NH:8][C:7]4=[O:18])[CH2:31][CH2:30]2)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 155426362a-(3-Formylpropyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-oneHCID 183773201-(1-Indanyl)piperazine hydrochloride

Product 1

HCID 183773382a-(4-(4-(1-Indanyl)-piperazin-1-yl)butyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2a-(3-Formylpropyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one (210 mg, 0.90 mmol), 1-(1-indanyl)piperazine hydrochloride (270 mg, 1.0 mmol), acetic acid (540 mg, 9.0 mmol) and sodium triacetoxyborohydride (380 mg, 1.8 mmol) were stirred at room temperature for 20 hours in 1,2-dichloroethane (3 ml). 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, the solvent was removed by evaporation under a reduced pressure, and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 430 mg (1.0 mmol, 100% in yield) of the title compound.

Workup

  1. washwashed with sodium hydroxide aqueous solution (1 N) and saturated brine
  2. dry with materialdried with anhydrous sodium sulfate
  3. customthe solvent was removed by evaporation under a reduced pressure
  4. customthe thus obtained material was separated
  5. custompurified by a silica gel column chromatography
  6. customto obtain

Sources & evidence

ORD record
ord-66b8e5cd9fde469585130f737a952d3e
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

Loading…