Piperidin-4-ol → HCID 19867675, compound

HRID 1199060Notes

Reaction equation

HRID 1199060 reaction equation
[CH3:1][O:2][C:3]1[N:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([N:13]3[C:21](=[O:22])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]3[O:23][CH2:24][C:25](O)=[O:26])=[N:10]2)=[CH:5][CH:4]=1.[OH:28][CH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>CN(C)C=O>[OH:28][CH:29]1[CH2:34][CH2:33][N:32]([C:25](=[O:26])[CH2:24][O:23][CH:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21](=[O:22])[N:13]2[C:9]2[CH:8]=[CH:7][C:6]3[C:11](=[N:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[N:10]=2)[CH2:31][CH2:30]1

Participants

4

Reactant 2

HCID 79341Piperidin-4-olHCID 19867644HCID 19867644, compound

Product 1

HCID 19867675HCID 19867675, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The procedure is as in Example 44, but starting with [2-(7-methoxy-1,8-napthyridin-2-yl)-3-oxo-1-isoindolinyloxy] acetic acid (3.5 g) in anhydrous dimethylformamide (70 cc), N,'-carbonyldiimidazole (1.6 g) and 4-hydroxypiperidine (0.82 g). After recrystallization in ethanol, 3-[2-(4-hydroxy-1-piperidyl)-2-oxoethoxy]-2-(7-methoxy-1,8-naphthyridin-2-yl)-1-isoindolinone (3.7 g), m.p. 167° C., is obtained.

Workup

  1. customAfter recrystallization in ethanol

Sources & evidence

ORD record
ord-4de0d0e267674a099f8fd601facfc9d3
Source dataset
uspto-grants-1990_02
Patent number
US04898871

Reaction notes

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