2-Methylpiperidine → 2-Methyl-1-(2-propynyl)piperidine

HRID 1808695Notes

Reaction equation

HRID 1808695 reaction equation
[CH2:1](Cl)[C:2]#[CH:3].[CH3:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][NH:7]1>CO>[CH3:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][N:7]1[CH2:3][C:2]#[CH:1]

Participants

4

Reactant 2

HCID 79742-MethylpiperidineHCID 122213-Chloro-1-propyne

Product 1

HCID 5789632-Methyl-1-(2-propynyl)piperidineYield 22.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A flask was charged with propargyl chloride (17.27 g, 0.232 mol, 70 wt % in toluene) in dry methanol (21 mL) under nitrogen atmosphere. (+/−)-2-Methyl-piperidine (55 mL, 0.46 mol) in dry methanol (43 mL) was added via drop-wise addition over 30 minutes. The material was stirred overnight. The mixture was placed on a rotovap and about half the volume of methanol was stripped, providing a precipitate. The solid precipitate was removed by filtration, rinsing through with ether (150 mL). The filtrite was placed on the rotovap and concentrated. Another small amount of precipitate was removed by filtration. The remaining oily product was purified by distillation providing 7.23 g (bp=180-185° C.) of (+/−)-2-methyl-1-prop-2-ynyl-piperidine as a clear mobile oil.

Workup

  1. customproviding a precipitate
  2. customThe solid precipitate was removed by filtration
  3. washrinsing through with ether (150 mL)
  4. concentrationconcentrated
  5. customAnother small amount of precipitate was removed by filtration
  6. distillationThe remaining oily product was purified by distillation

Sources & evidence

ORD record
ord-de45382a5a8c4d779eb0f2e7eb1aae8d
Source dataset
uspto-grants-2013_01
Patent number
US08361962B2

Reaction notes

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