Hydrochloric Acid → Ethyl 3-(2,6-dimethylpiperidino)propionate hydrochloride

HRID 1029489Notes

Reaction equation

HRID 1029489 reaction equation
[CH:1]([N:4]([CH:12]([CH3:14])[CH3:13])[CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:3])[CH3:2].Br[CH2:16]CC(OCC)=O.CC1CCCC(C)N1.[ClH:31]>O.C(O)C>[ClH:31].[CH3:14][CH:12]1[CH2:13][CH2:16][CH2:2][CH:1]([CH3:3])[N:4]1[CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 68320Ethyl 3-bromopropionateHCID 68843NanofinHCID 15468050Ethyl 3-diisopropylaminopropionate

Product 1

HCID 19900443Ethyl 3-(2,6-dimethylpiperidino)propionate hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl 3-(2,6-dimethylpiperidino)propionate hydrochloride may be obtained by working according to the method described in Example 6 for the preparation of ethyl 3- diisopropylaminopropionate, but starting with ethyl 3bromopropionate (18.1 g), 2,6-dimethylpiperidine (27 cc) and ethanol (30 cc). The reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) and the residue obtained is taken up with water (50 cc) and 4N aqueous hydrochloric acid solution (30 cc). The aqueous phase is washed with ethyl ether (2×80 cc) and neutralized with 4N aqueous sodium hydroxide solution (40 cc). The insoluble oil is extracted with ethyl ether (3×120 cc); the organic extracts are then washed with water (2×80 cc) and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The residue is dissolved in ethyl ether (100 cc). A 4.5N solution (13.4 cc) of gaseous hydrochloric acid in ethyl ether is added to the solution obtained. A product precipitates. It is separated by filtration, washed and dried in the air. Ethyl 3-(2,6-dimetylpiperidino)-propionate hydrochloride (14.4 g), m.p. 146° C., is thereby obtained.

Workup

  1. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. customthe residue obtained
  3. washThe aqueous phase is washed with ethyl ether (2×80 cc)
  4. extractionThe insoluble oil is extracted with ethyl ether (3×120 cc)
  5. washthe organic extracts are then washed with water (2×80 cc)
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  7. dissolutionThe residue is dissolved in ethyl ether (100 cc)
  8. additionA 4.5N solution (13.4 cc) of gaseous hydrochloric acid in ethyl ether is added to the solution
  9. customobtained
  10. customA product precipitates
  11. customIt is separated by filtration
  12. washwashed
  13. customdried in the air

Sources & evidence

ORD record
ord-7b80141d678b4f3bb99a0cd9ca36e9a0
Source dataset
uspto-grants-1992_04
Patent number
US05102890

Reaction notes

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