Hydrochloric Acid → N-(2-PIPERIDIN-4-YL-ETHYL)-ACETAMIDE

HRID 1164504Notes

Reaction equation

HRID 1164504 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)(=[O:3])[CH3:2].Cl.[H][H]>C(O)C.[Pt]=O>[C:1]([NH:4][CH2:5][CH2:6][CH:7]1[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 255093N-(2-Pyridin-4-yl-ethyl)-acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 4712038N-(2-PIPERIDIN-4-YL-ETHYL)-ACETAMIDEYield 52.6%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

4-(2-Acetamidoethyl)pyridine (33 g.) in ethanol (250 ml.) was acidified to pH 4 with hydrochloric acid and hydrogenated at 60 p.s.i./60° C. over a platinum oxide catalyst for 18 hours, after which time the uptake of hydrogen was complete. The catalyst was then removed by filtration and the filtrate was treated with a solution of potassium hydroxide flakes in methanol (1.1 molar equivalents) and refiltered. The solvents were distilled off in vacuo, leaving a clear oil, which on standing gave 4-(2-acetamidoethyl)piperidine (18 g.) as a white solid, m.p. 60° C.

Workup

  1. customThe catalyst was then removed by filtration
  2. additionthe filtrate was treated with a solution of potassium hydroxide flakes in methanol (1.1 molar equivalents)
  3. distillationThe solvents were distilled off in vacuo
  4. customleaving a clear oil, which

Sources & evidence

ORD record
ord-0994c038048a4bcc94138d57bf444953
Source dataset
uspto-grants-1983_01
Patent number
US04370328

Reaction notes

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