Potassium Carbonate → ethyl-2-{1-[2-(piperidin-1-yl)ethyl]-1H-indol-3-yl}2-oxoacetate

HRID 1472937Notes

Reaction equation

HRID 1472937 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[CH2:10]([O:12][C:13](=[O:25])[C:14]([C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[NH:18][CH:17]=1)=[O:15])[CH3:11].C([O-])([O-])=O.[K+].[K+]>>[CH2:10]([O:12][C:13](=[O:25])[C:14]([C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]([CH2:2][CH2:3][N:4]2[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)[CH:17]=1)=[O:15])[CH3:11]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 748271-(2-Chloroethyl)piperidineHCID 101242Ethyl 3-indolylglyoxylate

Product 1

HCID 67254916ethyl-2-{1-[2-(piperidin-1-yl)ethyl]-1H-indol-3-yl}2-oxoacetateYield 66%

Procedure

The general procedure 1 was then followed using 1-(2-chloroethyl)piperidine (10 mmol, 1.5 g), ethyl-2-(1H-indol-3-yl)-2-oxoacetate (7 mmol, 1.5 g) and K2CO3 (10.9 mmol, 1.5 g). The purification was achieved by column chromatography (petrol-ether:ethylacetate:diethylamine 8:1:1) to yield ethyl-2-{1-[2-(piperidin-1-yl)ethyl]-1H-indol-3-yl}2-oxoacetate (4.6 mmol, 66%) as an pale yellow oil. IR {tilde over (ν)} [cm−1]=2936; 2857; 1730; 1638. EI-MS m/z (rel. int.)=328 (18.99%; M+•.). 1H NMR (300 MHz, CDCl3) 8.43 (m; 2H; indole-H); 7.35 (m; 3H; indole-H); 4.40 (q; 3J=7.1 Hz; 2H; OCH2CH3); 4.25 (t; 3J=6.8 Hz; 2H; indole-CH2CH2N); 2.72 (t; 3J=6.8 Hz; 2H; indole-CH2CH2N); 2.43 (m; 4H; piperidin-CH2(C-2+6)); 1.57 (m; 4H; piperidin-CH2(C-3+5)); 1.43 (m; 5H; piperidin-CH2(C-4)+OCH2CH3).

Workup

  1. customThe purification

Sources & evidence

ORD record
ord-ba98dfc81b9c4678806811896285d3de
Source dataset
uspto-grants-2015_04
Patent number
US09012659B2

Reaction notes

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