Ethyl bromoacetate → (4-[3-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-piperazin-1-yl}-acetic acid ethyl ester

HRID 1836147Notes

Reaction equation

HRID 1836147 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][C:10]2[C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[NH:12][C:11]=2[CH:19]=[O:20])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH2:21]([O:23][C:24](=[O:27])[CH2:25]Br)[CH3:22].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:21]([O:23][C:24](=[O:27])[CH2:25][N:4]1[CH2:5][CH2:6][N:1]([CH2:7][CH2:8][CH2:9][C:10]2[C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[NH:12][C:11]=2[CH:19]=[O:20])[CH2:2][CH2:3]1)[CH3:22]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 234988213-(3-piperazin-1-yl-propyl)-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde

Product 1

HCID 86588564(4-[3-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-piperazin-1-yl}-acetic acid ethyl esterYield 62.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(3-Piperazin-1-yl-propyl)-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde (170 mg, 0.62 mmol), prepared as described in Example 8, was mixed with bromo-acetic acid ethyl ester (89 ml, 0.8 mmol, 1.3 eq.) and potassium carbonate (342 mg, 2.5 mmol, 4 eq.) in dimethylformamide. The mixture was stirred at room temperature overnight. The salt was filtered out and the filterate was rotary evaporated and purified by flash chromatography, eluting with (dichloromethane/methanol 40/1, 30/1) to give 140 mg of {(4-[3-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-piperazin-1-yl}-acetic acid ethyl ester.

Workup

  1. filtrationThe salt was filtered out
  2. customthe filterate was rotary evaporated
  3. custompurified by flash chromatography
  4. washeluting with (dichloromethane/methanol 40/1, 30/1)

Sources & evidence

ORD record
ord-e6dc07a01b004d9a94067b45193f28cd
Source dataset
uspto-grants-2004_08
Patent number
US06777417B2

Reaction notes

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