Dichloromethane → Methyl N,N-dibutyl-beta-alaninate

HRID 400210Notes

Reaction equation

HRID 400210 reaction equation
[CH2:1]([NH:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[C:10]([O:14][CH3:15])(=[O:13])[CH:11]=[CH2:12].ClCCl>CO>[CH2:1]([N:5]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:12][CH2:11][C:10]([O:14][CH3:15])=[O:13])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7294Methyl AcrylateHCID 8148Dibutylamine

Product 1

HCID 104456Methyl N,N-dibutyl-beta-alaninateYield 94.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A! A solution of dibutylamine (1 l, 5.88 moles) in methanol (2.35 l), kept under stirring at 50° C., was slowly added dropwise with methyl acrilate (1.051 l, 11.76 moles). The mixture was then brought to room temperature and kept under stirring for 1 hour, thereafter 1.174 l of dichloromethane were added and the product extracted with 4.7 l of 3N HCl. The organic phase was washed with water (3×2.35 l). The aqueous phase was brought to pH-9 with 5N sodium hydrate and extracted with dichloromethane (2×2.35 l). The organic phase was washed with 2.35 l of distilled water, then anhydrified over sodium sulfate and evaporated under vacuum thus obtaining 1197 g of methyl N,N-dibutyl-3-amino-propionate (yield: 94.5%) as a pale yellow oil which was used as such in the next step.

Workup

  1. customwas then brought to room temperature
  2. stirringunder stirring for 1 hour
  3. extractionthe product extracted with 4.7 l of 3N HCl
  4. washThe organic phase was washed with water (3×2.35 l)
  5. extractionextracted with dichloromethane (2×2.35 l)
  6. washThe organic phase was washed with 2.35 l of distilled water
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-7485e8b7d4804c5f9cdf0e54f44a91de
Source dataset
uspto-grants-1998_10
Patent number
US05827881

Reaction notes

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