Sodium Chloride → HCID 23345215, compound

HRID 1856472Notes

Reaction equation

HRID 1856472 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]1[C:16](=O)[CH2:15][CH2:14][CH:10]([C:11](O)=[O:12])[CH:9]1[C:18]1[CH:23]=[CH:22][C:21]2[O:24][CH2:25][O:26][C:20]=2[CH:19]=1.[Cl-].[Na+].[OH-].[Na+]>O1CCCC1>[CH3:7][N:8]1[CH2:16][CH2:15][CH2:14][CH:10]([CH2:11][OH:12])[CH:9]1[C:18]1[CH:23]=[CH:22][C:21]2[O:24][CH2:25][O:26][C:20]=2[CH:19]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 13416739HCID 13416739, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 23345215HCID 23345215, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a flask equipped with stirrer, dropping funnel and under a nitrogen atmosphere there is added 4.8 g. (0.126 mole) of lithium aluminum hydride to 250 ml. of anhydrous tetrahydrofuran. The resulting suspension is stirred and treated dropwise with a solution of 10.0 g. (0.036 mole) of 1-methyl-2-(3,4-methylenedioxyphenyl)-6-oxonipecotic acid in anhydrous tetrahydrofuran at such a rate that reflux occurs. The mixture is then stirred and refluxed for about 24 hours, cooled in an icebath and treated successively with 5 ml. of saturated sodium chloride solution, 5 ml. of 15% sodium hydroxide and 15 ml. of water and after separation stirred for an additional 2 hours. The resulting solid is filtered off and washed with tetrahydrofuran. The combined filtrates are then concentrated to yield 1-methyl-2-(3,4-methylenedioxyphenyl)-3-piperidinemethanol as an oil. The product is then dissolved in anhydrous methanol and saturated with dry hydrogen chloride gas. The solution is then concentrated to about 12 ml. and approximately 60 ml. of diethyl ether is then added. After stirring for 2 hours at room temperature the resultant solid is filtered off to give the hydrochloride salt of the title compound; m.p. 198° to 200° C.

Workup

  1. customTo a flask equipped with stirrer
  2. additionunder a nitrogen atmosphere there is added 4.8 g
  3. additiontreated dropwise with a solution of 10.0 g
  4. stirringThe mixture is then stirred
  5. temperaturerefluxed for about 24 hours
  6. temperaturecooled in an icebath
  7. additiontreated successively with 5 ml
  8. customof water and after separation
  9. stirringstirred for an additional 2 hours
  10. filtrationThe resulting solid is filtered off
  11. washwashed with tetrahydrofuran
  12. concentrationThe combined filtrates are then concentrated

Sources & evidence

ORD record
ord-8e5fdfc59aa74727b3029a3c71eb95b8
Source dataset
uspto-grants-1980_08
Patent number
US04219560

Reaction notes

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