1-(2-Methoxyphenyl)piperazine → 6-Acetoxy-2a-[4-(2-methoxyphenylpiperazinyl)butyl]-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

HRID 276914Notes

Reaction equation

HRID 276914 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:11]2[NH:10][C:9](=[O:14])[C:8]3([CH2:18][CH2:19][CH2:20][CH2:21]Br)[CH2:15][CH2:16][CH2:17][C:6]=1[C:7]=23)(=[O:3])[CH3:2].[CH3:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1N1CCNCC1.[CH:37]([N:40](CC)[CH:41]([CH3:43])C)([CH3:39])C.C[N:47](C=O)C>>[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:11]2[NH:10][C:9](=[O:14])[C:8]3([CH2:18][CH2:19][CH2:20][CH2:21][N:47]4[CH2:43][CH2:41][NH:40][CH2:37][CH:39]4[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[O:24][CH3:23])[CH2:15][CH2:16][CH2:17][C:6]=1[C:7]=23)(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 226295546-Acetoxy-2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

Product 1

HCID 226295506-Acetoxy-2a-[4-(2-methoxyphenylpiperazinyl)butyl]-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-oneYield 36%

Procedure

A 2 ml portion of DMF solution of 300 mg (0.82 mmol) 6-acetoxy-2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one (1.0 g, 5.8 mmol) was mixed with 315 mg (1.64 mmol) of 2-methoxyphenylpiperazine and 0.57 ml (3.28 mmol) of N,N-diisopropylethylamine, and the mixture was stirred overnight at a room temperature. The reaction solution was extracted with ethyl acetate and washed with water. After drying (Na2SO4), the solvent was evaporated under a reduced pressure, and the thus obtained oily substance was purified by a silica gel column chromatography (80 cc; elution with chloroform-methanol=30:1) to obtain 143 mg of the title compound (36% in yield).

Workup

  1. extractionThe reaction solution was extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialAfter drying (Na2SO4)
  4. customthe solvent was evaporated under a reduced pressure
  5. customthe thus obtained oily substance was purified by a silica gel column chromatography (80 cc; elution with chloroform-methanol=30:1)

Sources & evidence

ORD record
ord-ec34f6e6d6e6426ea9cb7164e0ee8f32
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Reaction notes

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