1-[3-(4-Benzyloxycoumarin-7-yloxy)-2-hydroxypropyl]-4-(4-chlorobenzyl)piperazine → 1-(4-Chlorobenzyl)-4-[2-hydroxy-3-(4-hydroxycoumarin-7-yloxy)propyl]piperazine

HRID 444216Notes

Reaction equation

HRID 444216 reaction equation
C([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH2:20][CH:21]([OH:37])[CH2:22][N:23]3[CH2:28][CH2:27][N:26]([CH2:29][C:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=4)[CH2:25][CH2:24]3)=[CH:16][CH:17]=2)[O:12][C:11](=[O:38])[CH:10]=1)C1C=CC=CC=1.[H][H]>CN(C=O)C.[Pd]>[Cl:36][C:33]1[CH:32]=[CH:31][C:30]([CH2:29][N:26]2[CH2:27][CH2:28][N:23]([CH2:22][CH:21]([OH:37])[CH2:20][O:19][C:15]3[CH:14]=[C:13]4[C:18]([C:9]([OH:8])=[CH:10][C:11](=[O:38])[O:12]4)=[CH:17][CH:16]=3)[CH2:24][CH2:25]2)=[CH:35][CH:34]=1

Participants

5

Reactant 2

HCID 134084121-[3-(4-Benzyloxycoumarin-7-yloxy)-2-hydroxypropyl]-4-(4-chlorobenzyl)piperazineHCID 178418361HCID 178418361, compound

Product 1

HCID 547107901-(4-Chlorobenzyl)-4-[2-hydroxy-3-(4-hydroxycoumarin-7-yloxy)propyl]piperazineYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-[3-(4-benzyloxycoumarin-7-yloxy)-2-hydroxypropyl]-4-(4-chlorobenzyl)piperazine (7 g) in dry DMF (80 ml) was hydrogenated at atmospheric pressure over 10% Pd/C catalyst till one equivalent of hydrogen was absorbed. Filtration and evaporation of the solvent in vacuo afforded an oily product which crystallized from ethanol/petrol to give 3.60 g (63%) of the title compound.

Workup

  1. customwas absorbed
  2. filtrationFiltration and evaporation of the solvent in vacuo
  3. customafforded an oily product which
  4. customcrystallized from ethanol/petrol

Sources & evidence

ORD record
ord-ff1079daf08a4f1a926e9a94b831292e
Source dataset
uspto-grants-1981_04
Patent number
US04263299

Reaction notes

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