Dimethylamine → Methyl 2-benzyl-3-dimethylaminopropionate

HRID 2309015Notes

Reaction equation

HRID 2309015 reaction equation
[CH2:1]([C:8](=[CH2:13])[C:9]([O:11][CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:14][NH:15][CH3:16]>CO>[CH2:1]([CH:8]([CH2:13][N:15]([CH3:16])[CH3:14])[C:9]([O:11][CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 575761Methyl 2-benzylprop-2-enoate

Product 1

HCID 13653933Methyl 2-benzyl-3-dimethylaminopropionate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 30.0 g of methyl α-benzylacrylate, prepared by the method of R. B. Miller and B. F. Smith, Synth. Commun. 3, 359 (1973) in methanol (50 ml) is added to a solution of dimethylamine (71.0 g) in methanol (210 ml), and the mixture is stirred at room temperature for 48 hours. The solvent is removed under reduced pressure to give methyl 2-benzyl-3-dimethylaminopropionate as a yellow oil, used without purification in the next synthetic step; NMR: δ7.14 (s, 5H), 3.52 (s, 3H), 2.82 (m, 3H), 2.17 (s, 6H), 2.63-2.17 (m, remaining H).

Workup

  1. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-4a298d1770b34240a2ffdc5ca0c9648a
Source dataset
uspto-grants-1987_09
Patent number
US04692469

Reaction notes

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