N-(2,3-Epoxypropyl)phthalimide → 2-[2-Hydroxy-3-[3-(1-piperidylmethyl)benzyloxy]propyl]-1H-isoindole-1,3-dione

HRID 542780Notes

Reaction equation

HRID 542780 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH2:11][OH:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:16]1[CH2:30][CH:17]1[CH2:18][N:19]1[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]2[C:20]1=[O:29]>>[OH:16][CH:17]([CH2:30][O:12][CH2:11][C:10]1[CH:13]=[CH:14][CH:15]=[C:8]([CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:9]=1)[CH2:18][N:19]1[C:20](=[O:29])[C:21]2[C:22](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]1=[O:24]

Participants

3

Reactant 2

HCID 21601N-(2,3-Epoxypropyl)phthalimideHCID 7164645(3-((Piperidin-1-yl)methyl)phenyl)methanol

Product 1

HCID 135354762-[2-Hydroxy-3-[3-(1-piperidylmethyl)benzyloxy]propyl]-1H-isoindole-1,3-dioneYield 42.1%

Conditions

Temperature
130 °C

Procedure

A mixture of 10.25 g (0.05 mol) of 3-(1-piperidylmethyl)-benzyl alcohol and 10.15 g (0.05 mol) of N-(2,3-epoxypropyl)-phthalimide is stirred under nitrogen for 80 minutes at 130° C. The viscous resin obtained is chromatographed on silica gel, using methylene chloride/methanol 9:1. The main fraction yields 8.60 g (42%) of the title compound in the form of a light brown oil after concentration by evaporation.

Workup

  1. customThe viscous resin obtained
  2. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-ce286276aa6e411cbdee0f5aea581459
Source dataset
uspto-grants-1987_04
Patent number
US04659721

Reaction notes

Loading…