Ethyl bromoacetate → N-Benzyl-4-(carbethoxymethoxy)-piperidine

HRID 1389760Notes

Reaction equation

HRID 1389760 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 784611-Benzylpiperidin-4-olHCID 178418361HCID 178418361, compound

Product 1

HCID 20295373N-Benzyl-4-(carbethoxymethoxy)-piperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-benzyl-4-hydroxy-piperidine (19.2 g) in dry tetrahydrofuran (100 ml), sodium hydride (2.4 g, 0.1 mole) was added and the mixture was refluxed until evolution of hydrogen ceased (1 hour). A solution of ethyl bromoacetate (18.4 g) in dry tetrahydrofuran (20 ml) was added and the mixture was refluxed for 3 hours. After standing over night, the solvent was removed in vacuo and the residue was extracted with light petroleum. The extract was concentrated to a sirup which was distilled at 0.1 mm Hg to give (A) as a colourless oil with b.p. 140°-145° C.

Workup

  1. custom(1 hour)
  2. temperaturethe mixture was refluxed for 3 hours
  3. waitAfter standing over night
  4. customthe solvent was removed in vacuo
  5. extractionthe residue was extracted with light petroleum
  6. concentrationThe extract was concentrated to a sirup which
  7. distillationwas distilled at 0.1 mm Hg

Sources & evidence

ORD record
ord-b2557c8991864fbfa05a943f33a45604
Source dataset
uspto-grants-1981_01
Patent number
US04246262

Reaction notes

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