Dimethylamine → 2-Dimethylaminomethyl-acrylic acid methyl ester

HRID 1038073Notes

Reaction equation

HRID 1038073 reaction equation
[CH3:1][O:2][C:3](=[O:8])[C:4]([CH2:6]Br)=[CH2:5].[CH3:9][NH:10][CH3:11].C1COCC1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:1][O:2][C:3](=[O:8])[C:4]([CH2:6][N:10]([CH3:11])[CH3:9])=[CH2:5]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 5210932-Propenoic acid, 2-(bromomethyl)-, methyl ester

Product 1

HCID 206696872-Dimethylaminomethyl-acrylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-bromomethyl-acrylic acid methyl ester (1 g, 5.59 mmol) in dry CH3CN (20 ml) was added 2M solution of dimethylamine in THF (3.07 ml, 6.14 mmol) followed by K2CO3 (0.93 g, 6.7 mmol). The reaction mixture was stirred overnight, filtered and washed with CH2Cl2. The filtrate was concentrated. The crude product was used in next reaction without further purification.

Workup

  1. filtrationfiltered
  2. washwashed with CH2Cl2
  3. concentrationThe filtrate was concentrated
  4. customThe crude product was used in next reaction without further purification

Sources & evidence

ORD record
ord-1bb20791307e46b8a6e16c1945d357b2
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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