1-(2-Chloroethyl)piperidine → HCID 18422073, compound

HRID 1281712Notes

Reaction equation

HRID 1281712 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[C:5]([NH:7][C:8]1[CH:9]=[C:10]([NH:15][C:16]([C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[N:24]=[CH:23][CH:22]=[CH:21]3)=[O:17])[CH:11]=[CH:12][C:13]=1[CH3:14])=[O:6].[N:31]1([CH2:37][CH2:38]Cl)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>>[N:31]1([CH2:37][CH2:38][O:1][C:2]2[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=2)[C:5]([NH:7][C:8]2[CH:9]=[C:10]([NH:15][C:16]([C:18]3[CH:19]=[C:20]4[C:25](=[CH:26][CH:27]=3)[N:24]=[CH:23][CH:22]=[CH:21]4)=[O:17])[CH:11]=[CH:12][C:13]=2[CH3:14])=[O:6])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

3

Reactant 2

HCID 748271-(2-Chloroethyl)piperidineHCID 18422129HCID 18422129, compound

Product 1

HCID 18422073HCID 18422073, compoundYield 55%

Procedure

Using an analogous procedure to that described in Example 7, N-[3-(3-hydroxybenzamido)-4-methylphenyl]quinoline-6-carboxamide was reacted with 2-piperidinoethyl chloride to give the title compound in 55% yield; NMR Spectrum: (DMSOd6) 1.39 (m, 2H), 1.49 (s, 4H), 2.2 (s, 3H), 2.42 (s, 4H), 2.65 (t, 2H), 4.15 (t, 2H), 7.15 (m, 1H), 7.26 (d, 1H), 7.41 (t, 1H), 7.55 (m, 2H), 7.62 (m,2H),7.86 (s, 1H), 8.12 (d, 1H), 8.24 (m, 1H), 8.52 (m, 1H), 8.61 (s, 1H), 8.99 (d, 1H), 9.89 (s, 1H), 10.48 (s, 1H); Mass Spectrum: M+H+ 509.

Sources & evidence

ORD record
ord-399288f8f1eb4f3dbd9d72798856111f
Source dataset
uspto-grants-2002_09
Patent number
US06455520B1

Reaction notes

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