Benzeneethanamine, 3,4-bis(phenylmethoxy)-, hydrochloride (1:1) → N-[2-(3,4-dibenzyloxyphenyl)ethyl]-1-methyl-3-(3-carbamoylphenyl)propylamine

HRID 638642Notes

Reaction equation

HRID 638642 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:13][CH2:14][NH2:15])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O=[C:28]([CH3:40])[CH2:29][CH2:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C:34]([NH2:36])=[O:35].C([BH3-])#N.[Na+]>CO>[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH2:13][CH2:14][NH:15][CH:28]([CH3:40])[CH2:29][CH2:30][C:31]2[CH:39]=[CH:38][CH:37]=[C:33]([C:34](=[O:35])[NH2:36])[CH:32]=2)[CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 2723941Benzeneethanamine, 3,4-bis(phenylmethoxy)-, hydrochloride (1:1)HCID 5003444Sodium cyanoborohydrideHCID 135636403-(3'-Oxobutyl)benzamide

Product 1

HCID 70424681N-[2-(3,4-dibenzyloxyphenyl)ethyl]-1-methyl-3-(3-carbamoylphenyl)propylamineYield 81.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.61 g of 3,4-dibenzyloxyphenethylamine hydrochloride and 2.70 g of 3-(3'-oxobutyl)benzamide were dissolved in 50 ml of methanol, to which was added 0.47 g of sodium cyanoborohydride. The reaction was allowed to stand at room temperature for 15 hours. Then, the solvent was distilled off and the residue was extracted with 300 ml of ethyl acetate. The organic phase was washed with water and dried with anhydrous sodium sulfate. The solvent was distilled off and the residue was subjected to silica gel chromatography (solvent chloroform:ethanol:acetic acid=90:8:2) to obtain 2.91 g of N-[2-(3,4-dibenzyloxyphenyl)ethyl]-1-methyl-3-(3-carbamoylphenyl)propylamine as a viscous oil.

Workup

  1. distillationThen, the solvent was distilled off
  2. extractionthe residue was extracted with 300 ml of ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried with anhydrous sodium sulfate
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-ed7bc6b02368483f9319c458f3fc45e3
Source dataset
uspto-grants-1985_12
Patent number
US04562206

Reaction notes

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