Diethyl Ether → HCID 13604904, compound

HRID 1981545Notes

Reaction equation

HRID 1981545 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([N:11]2[CH2:16][CH2:15][CH2:14][CH:13]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=3)[CH2:12]2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].C(OCC)C>O1CCCC1>[C:1]1([CH2:7][CH2:8][CH2:9][N:11]2[CH2:16][CH2:15][CH2:14][CH:13]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=3)[CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 136049031-(3-Phenylpropionyl)-3-(3-methoxyphenyl)piperidineHCID 21226445Aluminium lithium hydride

Product 1

HCID 13604904HCID 13604904, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The 1-(3-phenylpropionyl)-3-(3-methoxyphenyl)-piperidine was dissolved in 150 ml of dry tetrahydrofuran, and the solution was added to a suspension of 8.59 g (226 mmole) of lithium aluminum hydride in 150 ml of dry tetrahydrofuran, at room temperature. The resulting mixture was heated under reflux for 1 hour and then it was cooled in an ice-bath. To the cooled mixture was added, dropwise, with stirring, 43 ml of 3% aqueous sodium hydroxide, followed by 400 ml of diethyl ether. Stirring was continued for 45 minutes, and then the mixture was filtered. The filtrate was evaporated in vacuo to give 18.4 g of material.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperatureit was cooled in an ice-bath
  4. additionTo the cooled mixture was added
  5. stirringStirring
  6. filtrationthe mixture was filtered
  7. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-9af38bb16e7543e898bd8e2b110983fb
Source dataset
uspto-grants-1986_06
Patent number
US04593037

Reaction notes

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