Methyl 2-(2-chloroethoxy)benzoate → HCID 10161929, compound

HRID 457794Notes

Reaction equation

HRID 457794 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[CH:9]1.C[O:24][C:25](=[O:36])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[O:32][CH2:33][CH2:34]Cl>>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]2[CH2:22][CH2:21][N:20]([CH2:34][CH2:33][O:32][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[C:25]([OH:36])=[O:24])[CH2:19][CH2:18]2)=[CH:9]1

Participants

3

Reactant 2

HCID 9837283Methyl 2-(2-chloroethoxy)benzoateHCID 17964346HCID 17964346, compound

Product 1

HCID 10161929HCID 10161929, compound

Procedure

This compound was prepared following the procedure described in example 13 (part D) starting with 3 g (0.01 mol) of 1-(2-[1,3]dioxolan-2-yl-ethyl)-3-piperidin-4-yl-1H-indole and 2.8 g (0.013 mol) of 2-(2-chloro-ethoxy)-benzoic acid methyl ester. The crude mixture was purified by flash chromatography over silica gel affording 1.86 g (40% of yield) of 2-(2-{4-[1-(2-[1,3]dioxolan-2-yl-ethyl-1H-indol-3-yl]-piperidin-1-yl}-ethoxy)-benzoic acid.

Workup

  1. customThis compound was prepared
  2. customThe crude mixture was purified by flash chromatography over silica gel affording 1.86 g (40% of yield) of 2-(2-{4-[1-(2-[1,3]dioxolan-2-yl-ethyl-1H-indol-3-yl]-piperidin-1-yl}-ethoxy)-benzoic acid

Sources & evidence

ORD record
ord-62f4dfc7a8044692b8f30f0381f7476b
Source dataset
uspto-grants-2007_03
Patent number
US07189741B2

Reaction notes

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