Hydroxide → HCID 23469688, compound

HRID 128357Notes

Reaction equation

HRID 128357 reaction equation
[Br:1][C:2]1[C:3]2[C:4]3[C:8](=[CH:9][CH:10]=1)[N:7]=[C:6]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)[C:5]=3[CH:17]=[CH:18][CH:19]=2.O.[OH-].[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)(Cl)Cl>[C:22]([N:14]1[CH2:13][CH2:12][N:11]([C:6]2[C:5]3[CH:17]=[CH:18][CH:19]=[C:3]4[C:4]=3[C:8](=[CH:9][CH:10]=[C:2]4[Br:1])[N:7]=2)[CH2:16][CH2:15]1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 961HydroxideHCID 962WaterHCID 7412Benzoyl chloride2×HCID 23469695HCID 23469695, compound

Product 1

HCID 23469688HCID 23469688, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture consisting of 7.1 g. of 1-(6-bromobenz-[cd]indol-2-yl)piperazine, 75 ml. of water, and 75 ml. of chloroform is stirred vigorously as 10 ml. of 5 N soidum hydroxide is added, followed by 5 g. of benzoyl chloride, in six portions over a period of 10 minutes. The reaction mixture is stirred an additional 30 minutes after the completion of the benzoyl chloride addition. The chloroform layer is separated and dried over sodium sulrate. After separation from impurities by chromatography on an alumina column, the title compound is recrystallized from benzene-chloroform to yield orange flakes, melting at 237.5°-239° C.

Workup

  1. customThe chloroform layer is separated
  2. dry with materialdried over sodium sulrate
  3. customAfter separation from impurities by chromatography on an alumina column
  4. customthe title compound is recrystallized from benzene-chloroform
  5. customto yield orange flakes, melting at 237.5°-239° C.

Sources & evidence

ORD record
ord-aef35b71ed904d1ca07a9eaf99465da7
Source dataset
uspto-grants-1981_03
Patent number
US04259490

Reaction notes

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