Benzyl Bromide → Ethyl 3-(dibenzylamino)propanoate

HRID 1469299Notes

Reaction equation

HRID 1469299 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Cl.[CH2:8]([O:10][C:11](=[O:15])[CH2:12][CH2:13][NH2:14])[CH3:9].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(#N)C>[CH2:16]([N:14]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:13][CH2:12][C:11]([O:10][CH2:8][CH3:9])=[O:15])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 458475beta-Alanine, ethyl ester, hydrochloride

Product 1

HCID 44791227Ethyl 3-(dibenzylamino)propanoateYield 102.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Sodium carbonate (21.1 g, 199 mmol) was added to a suspension of β-alanine ethyl ester hydrochloride (10.2 g, 66.4 mmol) and benzyl bromide (16.2 mL, 136 mmol) in acetonitrile (265 mL). The reaction mixture was stirred at ambient temperature overnight and then filtered through a layer of CELITE filter aid. The filter cake was rinsed with acetonitrile (100 mL). The filtrate was concentrated under reduced pressure to provide 20.28 g of ethyl 3-dibenzylaminopropionate as a pale yellow oil.

Workup

  1. filtrationfiltered through a layer of CELITE
  2. filtrationfilter aid
  3. washThe filter cake was rinsed with acetonitrile (100 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-66398230e6534d0295ae55d92f61bb49
Source dataset
uspto-grants-2015_04
Patent number
US09006264B2

Reaction notes

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