1-Phenylpiperazine → HCID 19734253, compound

HRID 327084Notes

Reaction equation

HRID 327084 reaction equation
C1(C)C=CC(S(O[CH2:11][CH:12]2[NH:24][C:23](=[O:25])[C:21]3[C:22]4[C:14](=[CH:15][NH:16][C:17]=4[CH:18]=[CH:19][CH:20]=3)[CH2:13]2)(=O)=O)=CC=1.[C:27]1([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[C:27]1([N:33]2[CH2:38][CH2:37][N:36]([CH2:11][CH:12]3[NH:24][C:23](=[O:25])[C:21]4[C:22]5[C:14](=[CH:15][NH:16][C:17]=5[CH:18]=[CH:19][CH:20]=4)[CH2:13]3)[CH2:35][CH2:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

3

Reactant 2

HCID 70961-PhenylpiperazineHCID 19734224HCID 19734224, compound

Product 1

HCID 19734253HCID 19734253, compound

Conditions

Temperature
80 °C

Procedure

2.2 g of 4-(p-toluenesulfonyloxymethyl)-3,4,5,6-tetrahydro-6-oxo-1H-azepino[5,4,3-cd]indole (for preparation see Example 7E) were mixed with 9 ml of 1-phenylpiperazine, and the mixture was stirred at a temperature of 80° C. for 4 hours. Subsequent cooling resulted in the crude title compound crystallising out. It was filtered out and washed with a mixture of equal parts of methanol and water. Drying resulted in 1.7 g of 4-(4-phenyl-1-piperazinylmethyl)- 3,4,5,6-tetrahydro-6-oxo-1H-azepino[5,4,3-cd]indole with a melting point of 184° to 185° C.

Workup

  1. temperatureSubsequent cooling
  2. customresulted in the crude title compound
  3. customcrystallising out
  4. filtrationIt was filtered out
  5. washwashed with a mixture of equal parts of methanol and water
  6. customDrying
  7. customresulted in 1.7 g of 4-(4-phenyl-1-piperazinylmethyl)- 3,4,5,6-tetrahydro-6-oxo-1H-azepino[5,4,3-cd]indole with a melting point of 184° to 185° C.

Sources & evidence

ORD record
ord-5687032731a94ab78c21656a5b03c94f
Source dataset
uspto-grants-1993_12
Patent number
US05272143

Reaction notes

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