Diisopropylamine → Ethyl 4-diisopropylaminobutyrate

HRID 1029500Notes

Reaction equation

HRID 1029500 reaction equation
[CH:1]([NH:4][CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].Br[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(O)C>[CH:1]([N:4]([CH:5]([CH3:7])[CH3:6])[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 7912DiisopropylamineHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 19900433Ethyl 4-diisopropylaminobutyrateYield 21.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-diisopropylaminobutyrate may be obtained in the following manner: diisopropylamine (40.4 g) is added dropwise to a solution of ethyl 4-bromobutyrate (39 g) in ethanol (80 cc). The solution obtained is heated to reflux for 6 hours. After the insoluble material formed has been filtered off, the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The residue is taken up with distilled water (15 cc) and 4 N aqueous hydrochloric acid solution (100 cc). The aqueous phase is washed with ethyl ether (3×75 cc) and then alkalinized with 10 N aqueous sodium hydroxide solution. The oil formed is extracted with ethyl ether (3×75 cc). The organic phase obtained is concentrated to dryness under reduced pressure (2.7 kPa). Ethyl 4-diisopropylaminobutyrate (9.2 g) is thereby obtained in the form of an oil, which is employed in the crude state in the subsequent syntheses.

Workup

  1. customThe solution obtained
  2. temperatureis heated
  3. temperatureto reflux for 6 hours
  4. customAfter the insoluble material formed
  5. filtrationhas been filtered off
  6. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)
  7. washThe aqueous phase is washed with ethyl ether (3×75 cc)
  8. customThe oil formed
  9. extractionis extracted with ethyl ether (3×75 cc)
  10. customThe organic phase obtained
  11. concentrationis concentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-c80d78822dce493db7d88a0ee234263e
Source dataset
uspto-grants-1992_04
Patent number
US05102890

Reaction notes

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