Benzyl Bromide → Ethyl 3-(dibenzylamino)propanoate

HRID 2278941Notes

Reaction equation

HRID 2278941 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:10]([N:2]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 458475beta-Alanine, ethyl ester, hydrochloride

Product 1

HCID 44791227Ethyl 3-(dibenzylamino)propanoateYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of ethyl 3-aminopropanoate hydrochloride (80.0 g, 0.52 mol), benzylbromide (186.7 g, 1.1 mol) and K2CO3 (179.4 g, 1.3 mol) in MeCN (1 L) was heated at 40° C. overnight. The mixture was concentrated to dryness, poured into water, extracted with EtOAc (3×) and the combined organics were washed with brine, dried over Na2SO4 and purified via silica gel chromatography to give ethyl 3-(dibenzylamino)propanoate (150 g, 97%).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. additionpoured into water
  3. extractionextracted with EtOAc (3×)
  4. washthe combined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. custompurified via silica gel chromatography

Sources & evidence

ORD record
ord-e967364a5adb4228ae141c11dc6463b7
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

Loading…