Sodium hydride → HCID 14209206, compound

HRID 1199037Notes

Reaction equation

HRID 1199037 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]1.[H-].[Na+].Cl[CH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=[O:21])[N:13]1[C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[N:25][C:26]([Cl:32])=[CH:27][CH:28]=2)[N:23]=1>>[Cl:32][C:26]1[N:25]=[C:24]2[C:29]([CH:30]=[CH:31][C:22]([N:13]3[CH:12]([O:8][CH:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]3=[O:21])=[N:23]2)=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 660484-Piperidinol, 1-methyl-HCID 141824043-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone

Product 1

HCID 14209206HCID 14209206, compoundYield 19.7%

Procedure

Working in a manner similar to that described in Example 6, but starting with 1-methyl-4-piperidinol (4.3 g), sodium hydride (0.9 g) and 3-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone (12.4 g), and heating the reaction mixture for 90 minutes under reflux, 2-(7-chloro-1,8-naphthyridin-2-yl)-3-(1-methyl-4-piperidyloxy)-1-isoindolinone (3 g), m.p. 204° C., is obtained after recrystallization in ethanol.

Workup

  1. temperatureheating the reaction mixture for 90 minutes
  2. temperatureunder reflux

Sources & evidence

ORD record
ord-975fb1d1273545a2b206107efca965d2
Source dataset
uspto-grants-1990_02
Patent number
US04898871

Reaction notes

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