Ethyl Acrylate → HCID 58494030, compound

HRID 1942702Notes

Reaction equation

HRID 1942702 reaction equation
[Br:1][C:2]1[C:3]([CH2:15][CH3:16])=[C:4]([CH:8]=[C:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1.C1CCN2C(=NCCC2)CC1.[C:28]([O:32][CH2:33][CH3:34])(=[O:31])[CH:29]=[CH2:30]>C(#N)C>[Br:1][C:2]1[C:3]([CH2:15][CH3:16])=[C:4]([CH:8]=[C:9]2[CH2:10][CH2:11][N:12]([CH2:30][CH2:29][C:28]([O:32][CH2:33][CH3:34])=[O:31])[CH2:13][CH2:14]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8821Ethyl AcrylateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 58494028HCID 58494028, compound

Product 1

HCID 58494030HCID 58494030, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-[(3-bromo-2-ethylphenyl)methylidene]piperidine (D137) (1 g, 3.57 mmol) in Acetonitrile (10 mL) was added DBU (0.807 mL, 5.35 mmol) and ethyl 2-propenoate (0.429 g, 4.28 mmol). The reaction solution was heated to 60° C. for overnight. The solvent was removed in vacuo and the residue was diluted with ethyl acetate, washed with water, dried and concentrated to afford ethyl 3-{4-[(3-bromo-2-ethylphenyl)methylidene]-1-piperidinyl}propanoate (D138) (1.35 g), which was used directly without further purification. MS (ES): C19H26BrNO2 requires 379.1. found 380.1 (M+H+).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-67d610a51fd643c997e756c743c5ea0a
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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