Benzyl Bromide → Ethyl 3-(dibenzylamino)propanoate

HRID 715111Notes

Reaction equation

HRID 715111 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+]>C(#N)C>[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

Heat 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 acetonitrile (1 L) at 40° C. overnight. Concentrate the mixture to dryness, treat with water, extract with EtOAc (3×), wash the combined organics with brine, dry over Na2SO4, concentrate to dryness and purify via silica gel chromatography (Pet Ether/EtOAc, 50:1) to afford the title compound (150 g, 97% yield). 1H NMR (400 MHz, CDCl3): δ 7.35-7.21 (m, 10H), 4.09 (q, J=7.2 Hz, 2H), 3.58 (s, 4H), 2.82 (t, J=7.2 Hz, 2H), 2.50 (t, J=7.2 Hz, 2H), 1.21 (t, J=7.2 Hz, 3H).

Workup

  1. concentrationConcentrate the mixture to dryness
  2. additiontreat with water
  3. extractionextract with EtOAc (3×)
  4. washwash the combined organics with brine
  5. dry with materialdry over Na2SO4
  6. concentrationconcentrate to dryness
  7. custompurify via silica gel chromatography (Pet Ether/EtOAc, 50:1)

Sources & evidence

ORD record
ord-56b47705f4124c25b10e81340d0440e8
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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