Benzylamine → Ethyl 3-(benzylamino)-3-oxopropanoate

HRID 598221Notes

Reaction equation

HRID 598221 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([CH:11]([C:15](Cl)=[O:16])[C:12](Cl)=[O:13])C.C(N([CH2:23][CH3:24])CC)C.C(=O)(O)[O-:26].[Na+]>ClCCl>[O:16]=[C:15]([NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:11][C:12]([O:13][CH2:23][CH3:24])=[O:26]

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 109209242-Ethylpropanedioyl dichloride

Product 1

HCID 11379032Ethyl 3-(benzylamino)-3-oxopropanoateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzylamine (1.10 g, 10.3 mmol) and ethyl malonyl chloride (1.29 mL, 10.3 mmol) in dichloromethane (10 mL) was treated with triethylamine (1.44 mL, 10.3 mmol). The solution was stirred at ambient temperature for 1 h and then diluted with saturated aqueous sodium bicarbonate and extracted with ethyl acetate (3×20 mL). The combined organic portions were dried over magnesium sulfate, filtered, and concentrated in vacuo to obtain the title compound as a yellow oil (2.27 g, 100%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.55 (br. s., 1H), 7.24-7.36 (m, 5H), 4.45 (d, J=5.6 Hz, 2H), 4.17 (q, J=7.2 Hz, 2H), 3.31 (s, 2H), 1.27 (t, J=7.2 Hz, 3H). MS(ES+) m/e 222 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. dry with materialThe combined organic portions were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fac54f3536074f53a9498d3dd2e68117
Source dataset
uspto-grants-2011_03
Patent number
US07897612B2

Reaction notes

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