Diethyl Ether → Ethyl N,N-dibutyl-beta-alaninate

HRID 1603181Notes

Reaction equation

HRID 1603181 reaction equation
Br[CH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:9]([NH:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:11][CH3:12].C(OCC)C>CCCCC>[CH2:9]([N:13]([CH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8148DibutylamineHCID 68320Ethyl 3-bromopropionate

Product 1

HCID 88373Ethyl N,N-dibutyl-beta-alaninate

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

Ethyl 3-bromopropionate (18.0 g; 0.10 mol) was added carefully to di-n-butylamine (25.8 g; 0.20 mol), followed by stirring for 2 hours. Then diethyl ether (200 ml) and pentane (200 ml) were added. The precipitate was filtered off, the filtrate was evaporated and the residue was distilled at sub-atmospheric pressure. The yield was 7.0 g (31%).

Workup

  1. filtrationThe precipitate was filtered off
  2. customthe filtrate was evaporated
  3. distillationthe residue was distilled at sub-atmospheric pressure

Sources & evidence

ORD record
ord-a6d6605e9cbc42a8a1f05a78bf435d18
Source dataset
uspto-grants-1999_11
Patent number
US05986029

Reaction notes

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