Pyridine → HCID 2970864, compound

HRID 1418368Notes

Reaction equation

HRID 1418368 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[CH2:7]1[O:16][C:10]2([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[O:9][CH2:8]1.N1C=CC=CC=1>ClCCl>[CH2:7]1[O:16][C:10]2([CH2:15][CH2:14][N:13]([C:1](=[O:5])[CH2:2][CH2:3][CH3:4])[CH2:12][CH2:11]2)[O:9][CH2:8]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 8855Butyryl chlorideHCID 674351,4-Dioxa-8-azaspiro(4.5)decane

Product 1

HCID 2970864HCID 2970864, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

Butyryl chloride (0.53 g, 5 mmol) in dry dichloromethane (5 ml) was added dropwise with stirring to 4-piperidone ethylene ketal (0.72g, 5 mmol) and pyridine (0.5 ml) in dry dichloromethane (10 ml). The solution was stirred at 20° C. overnight then washed successively with dilute HCl, saturated sodium bicarbonate solution and water and dried (sodium sulphate). Evaporation of the solvent gave the product as a clear syrup (0.66 g). MS (+EI) 213 (M+), 1H NMR (CDCl3) 3.98 (4H, s), 3.70 (2H, t), 3.53 (2H, t), 2.33 (2H, t), 1.61-1.83 (6H, m), 0.97 (3H, t).

Workup

  1. washthen washed successively with dilute HCl, saturated sodium bicarbonate solution and water
  2. dry with materialdried (sodium sulphate)
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-82890ec885d441349298420957910f25
Source dataset
uspto-grants-1999_03
Patent number
US05883102

Reaction notes

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