Ethyl Acrylate → N-[3-[bis(phenylmethyl)amino]propyl]-beta-alanine, ethyl ester

HRID 1793333Notes

Reaction equation

HRID 1793333 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:20]([O:24][CH2:25][CH3:26])(=[O:23])[CH:21]=[CH2:22]>C(O)C>[C:7]1([CH2:6][N:5]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:4][CH2:3][CH2:2][NH:1][CH2:22][CH2:21][C:20]([O:24][CH2:25][CH3:26])=[O:23])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 8821Ethyl AcrylateHCID 114367481,3-Propanediamine, N,N-bis(phenylmethyl)-

Product 1

HCID 131725872N-[3-[bis(phenylmethyl)amino]propyl]-beta-alanine, ethyl esterYield 39.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Reaction under an argon flow. A mixture of 1-amino-3-dibenzylaminopropane (0.195 mol) in ethanol (225 ml) was stirred at room temperature. Ethyl propenoate (0.2 mol) was poured into the mixture and the reaction mixture was stirred overnight at room temperature. The solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/hexane/CH3OH 50/45/5). The desired fractions were collected and the solvent was evaporated, yielding 27 g of N-[3-[bis(phenylmethyl)amino]propyl]-β-alanine, ethyl ester (intermediate 52).

Workup

  1. customReaction under an argon flow
  2. stirringthe reaction mixture was stirred overnight at room temperature
  3. customThe solvent was evaporated
  4. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/hexane/CH3OH 50/45/5)
  5. customThe desired fractions were collected
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b5cf7d59486349e89fab2b0620de818e
Source dataset
uspto-grants-2006_07
Patent number
US07081453B2

Reaction notes

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