Acetyl chloride → N-Benzyl-4-(carbethoxymethoxy)-piperidine

HRID 329027Notes

Reaction equation

HRID 329027 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH2:5]([N:12]1[CH2:17][CH2:16][CH:15]([O:18][CH2:19][CH2:20][OH:21])[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C>C1C=CC=CC=1>[CH2:5]([N:12]1[CH2:13][CH2:14][CH:15]([O:18][CH2:19][C:20]([O:3][CH2:1][CH3:2])=[O:21])[CH2:16][CH2:17]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 202953472-((1-Benzylpiperidin-4-yl)oxy)ethanol

Product 1

HCID 20295373N-Benzyl-4-(carbethoxymethoxy)-piperidineYield 66%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

15.6 g (0.2 mole) of acetyl chloride were added dropwise while cooling at 20° C with an ice bath to a solution of 47 g (0.2 mole) of 2-(1-benzyl-4-piperidyloxy)-ethanol, prepared according to the step B of Example I, and 20.2 g (0.2 mole) of triethylamine in 300 ml of benzene and after standing for 48 hours at room temperature, the precipitate was removed by vacuum filtration. The benzene filtrate was washed with aqueous sodium bicarbonate solution, then water, dried and the benzene distilled off. The residue was distilled to obtain 36.5 g (66% yield) of ethyl 2-(1-benzyl-4-piperidyloxy)-acetate as a clear oil boiling at 160°-170° C at 0.1 mm Hg and having a refractive index nD20 = 1.512.

Workup

  1. customprepared
  2. customthe precipitate was removed by vacuum filtration
  3. washThe benzene filtrate was washed with aqueous sodium bicarbonate solution
  4. dry with materialwater, dried
  5. distillationthe benzene distilled off
  6. distillationThe residue was distilled

Sources & evidence

ORD record
ord-a1887121735d4623a5e1f2aebb99ca7d
Source dataset
uspto-grants-1977_04
Patent number
US04018922

Reaction notes

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