Hydrochloric Acid → Ethyl 3-diisopropylaminopropionate

HRID 1029480Notes

Reaction equation

HRID 1029480 reaction equation
Br[CH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH:9]([NH:12][CH:13]([CH3:15])[CH3:14])([CH3:11])[CH3:10].C(O)C.Cl>O>[CH:9]([N:12]([CH:13]([CH3:15])[CH3:14])[CH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 7912DiisopropylamineHCID 68320Ethyl 3-bromopropionate

Product 1

HCID 15468050Ethyl 3-diisopropylaminopropionate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

Ethyl 3-diisopropylaminopropionate may be obtained in the following manner: ethyl 3-bromopropionate (18.1 g) is introduced dropwise in the course of 30 minutes into a solution of diisopropylamine (28.5 cc) and ethanol (40 cc) maintained at a temperature of 25° C. The suspension obtained is heated to reflux for 4 hours. After being cooled, the reaction mixture is taken up with water (100 cc) and 4N aqueous hydrochloric acid solution (70 cc). After the mixture is washed with ethyl ether (100 cc), it is alkalinized to a pH in the region of 9 with 4N aqueous sodium hydroxide solution. The oil formed is extracted with methylene chloride (3×150 cc). After being washed with water (2×100 cc) and dried, the methylene chloride solution obtained is concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. Ethyl 3-diisopropylaminopropionate (11.6 g) is thereby obtained in the form of an oil, which is employed in the crude state in the subsequent syntheses.

Workup

  1. customThe suspension obtained
  2. temperatureis heated
  3. temperatureto reflux for 4 hours
  4. temperatureAfter being cooled
  5. washAfter the mixture is washed with ethyl ether (100 cc), it
  6. customThe oil formed
  7. extractionis extracted with methylene chloride (3×150 cc)
  8. washAfter being washed with water (2×100 cc)
  9. customdried
  10. customthe methylene chloride solution obtained
  11. concentrationis concentrated to dryness under reduced pressure (2.7 kPa) at 40° C

Sources & evidence

ORD record
ord-1a786621b4104cb59de262bed88c287c
Source dataset
uspto-grants-1992_04
Patent number
US05102890

Reaction notes

Loading…