1H-Indole-5-Carboxylic Acid → 1-(Indole-5-carbonyl)-4-[2-(4-nitrophenyl)ethyl]piperazine

HRID 1086856Notes

Reaction equation

HRID 1086856 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:18][CH:17]=1)([O-:15])=[O:14]>>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([N:27]3[CH2:28][CH2:29][N:24]([CH2:23][CH2:22][C:19]4[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:21][CH:20]=4)[CH2:25][CH2:26]3)=[O:12])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

3

Reactant 2

HCID 742801H-Indole-5-Carboxylic AcidHCID 149859651-[2-(4-Nitrophenyl)ethyl]piperazine

Product 1

HCID 149860001-(Indole-5-carbonyl)-4-[2-(4-nitrophenyl)ethyl]piperazine

Procedure

In the manner described in Example 24, indole-5-carboxylic acid (100 mg, 0.62 mmol) and 1-[2-(4-nitrophenyl)ethyl]piperazine (151 mg, 0.64 mmol) gave, after purification by flash column chromatography on silica gel, eluting with CH2Cl2 /MeOH/NH3 ; 95:5:0.5 and trituration with hexane/EtOAc, the piperazine (38 mg, 16%), mp 204°-206° C.

Workup

  1. customgave
  2. customafter purification by flash column chromatography on silica gel
  3. washeluting with CH2Cl2 /MeOH/NH3

Sources & evidence

ORD record
ord-250d25133e02467090b1826a23fbd0cf
Source dataset
uspto-grants-1991_07
Patent number
US05032598

Reaction notes

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