Ethanol → N,N-Dimethyl-4-(1,2,3,4-tetrahydro-isoquinolin-7-yloxy)-benzamide

HRID 1876290Notes

Reaction equation

HRID 1876290 reaction equation
C(OC([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][C:15]([O:21][C:22]3[CH:27]=[CH:26][C:25]([C:28](=[O:32])[N:29]([CH3:31])[CH3:30])=[CH:24][CH:23]=3)=[CH:16][CH:17]=2)[CH2:12]1)=O)C1C=CC=CC=1.C(O)C>[Pd].[H][H]>[CH3:30][N:29]([CH3:31])[C:28](=[O:32])[C:25]1[CH:24]=[CH:23][C:22]([O:21][C:15]2[CH:14]=[C:13]3[C:18]([CH2:19][CH2:20][NH:11][CH2:12]3)=[CH:17][CH:16]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 584939027-(4-Dimethylcarbamoyl-phenoxy)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester

Product 1

HCID 58493883N,N-Dimethyl-4-(1,2,3,4-tetrahydro-isoquinolin-7-yloxy)-benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 178418361HCID 178418361, compoundSolvent

Procedure

A mixture of 10% palladium on carbon (1.50 g), 7-(4-dimethylcarbamoyl-phenoxy)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (2 mL), and ethanol (200 mL) is shaken in hydrogen atmosphere (3 bar) at room temperature for 2 h. Then the catalyst is separated by filtration and the filtrate is concentrated. The residue is purified by chromatography on silica gel (methanol/methanol containing 1% ammionia 1:0→0:1) to furnish the title compound that is precipitated from dioxane with 6 M HCl in dioxane.

Workup

  1. customThen the catalyst is separated by filtration
  2. concentrationthe filtrate is concentrated
  3. customThe residue is purified by chromatography on silica gel (methanol/methanol containing 1% ammionia 1:0→0:1)

Sources & evidence

ORD record
ord-a27e83bd9fe247f788240b39a8d6ae52
Source dataset
uspto-grants-2012_11
Patent number
US08309597B2

Reaction notes

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