5-(3-Chloro-propoxy)-1H-indole → 1-(3-(Indol-5-yloxy)prop-1-yl)-4-hydroxy-4-(quinolin-3-yl)piperidine

HRID 1066084Notes

Reaction equation

HRID 1066084 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][CH2:11][CH2:12][CH2:13]Cl)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH:15][C:16]1([C:22]2[CH:23]=[N:24][C:25]3[C:30]([CH:31]=2)=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][CH2:11][CH2:12][CH2:13][N:19]3[CH2:20][CH2:21][C:16]([OH:15])([C:22]4[CH:23]=[N:24][C:25]5[C:30]([CH:31]=4)=[CH:29][CH:28]=[CH:27][CH:26]=5)[CH2:17][CH2:18]3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

3

Reactant 2

HCID 114994555-(3-Chloro-propoxy)-1H-indoleHCID 211980104-(Quinolin-3-yl)piperidin-4-ol

Product 1

HCID 99090351-(3-(Indol-5-yloxy)prop-1-yl)-4-hydroxy-4-(quinolin-3-yl)piperidineYield 45.6%

Procedure

Beginning with 0.275 gm (1.3 mMol) 3-chloropropyl indol-5-yl ether and 0.300 gm (1.3 mMol) 4-hydroxy-4-(quinolin-3-yl)piperidine, 0.238 gm (45%) of the title compound were recovered as an off-white solid.

Sources & evidence

ORD record
ord-ff839a0ac182457f900dabe568b32228
Source dataset
uspto-grants-2001_06
Patent number
US06242450B1

Reaction notes

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