Dibenzylamine → Ethyl 4-(Dibenzylamino)butanoate

HRID 1614057Notes

Reaction equation

HRID 1614057 reaction equation
I[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH2:10]([NH:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:18]([N:17]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7656DibenzylamineHCID 11430Potassium CarbonateHCID 10890062Ethyl 4-iodobutanoate

Product 1

HCID 13929784Ethyl 4-(Dibenzylamino)butanoateYield 83.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Mix ethyl 4-iodobutyrate (43.5 g, 0.18 mol), dibenzylamine (35.5 g, 0.18 mol), potassium carbonate (24.9 g, 0.18 mol) and ethanol (114 mL dried over 4A molecular sieves). Reflux for 24 hours then stir at room temperature for 48 hours. Add methylene chloride (100 mL) and filter. Evaporate the filtrate to a residue and purify by silica gel chromatography (methylene chloride) to give the title compound (47 g).

Workup

  1. temperatureReflux for 24 hours
  2. filtrationAdd methylene chloride (100 mL) and filter
  3. customEvaporate the filtrate to a residue
  4. custompurify by silica gel chromatography (methylene chloride)

Sources & evidence

ORD record
ord-ab824be86273434690521b5f2822d0c0
Source dataset
uspto-grants-1993_03
Patent number
US05194430

Reaction notes

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