Methyl 2-(2-chloroethoxy)benzoate → 2-(2-(4-(1-(2-(1,4-dioxan-2-yl)ethyl)-1H-indol-3-yl)piperidin-1-yl)ethoxy)benzoic acid

HRID 457837Notes

Reaction equation

HRID 457837 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][CH2:3][CH:2]1[CH2:7][CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[CH:10]1.C[O:25][C:26](=[O:37])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH2:34][CH2:35]Cl>>[O:1]1[CH2:6][CH2:5][O:4][CH2:3][CH:2]1[CH2:7][CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH:18]2[CH2:23][CH2:22][N:21]([CH2:35][CH2:34][O:33][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[C:26]([OH:37])=[O:25])[CH2:20][CH2:19]2)=[CH:10]1

Participants

3

Reactant 2

HCID 9837283Methyl 2-(2-chloroethoxy)benzoateHCID 179643591-(2-[1,4]dioxan-2-yl-ethyl)-3-piperidin-4-yl-1H-indole

Product 1

HCID 101405442-(2-(4-(1-(2-(1,4-dioxan-2-yl)ethyl)-1H-indol-3-yl)piperidin-1-yl)ethoxy)benzoic acid

Procedure

This compound was prepared following the procedure described in example 13 (part D) starting with 0.58 g (1.84 mmol) of 1-(2-[1,4]dioxan-2-yl-ethyl)-3-piperidin-4-yl-1H-indole (example 71, part B) and 0.51 g (2.39 mmol) of 2-(2-chloro-ethoxy)-benzoic acid methyl ester. After standard work-up and purification by flash chromatography over silica gel, 0.18 g (20% of yield) of the expected acid were obtained.

Workup

  1. customThis compound was prepared
  2. customAfter standard work-up and purification by flash chromatography

Sources & evidence

ORD record
ord-c0a53e3f9edb43fca8044520536dca47
Source dataset
uspto-grants-2007_03
Patent number
US07189741B2

Reaction notes

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