Water → 3-(2-Tetrahydropyranyloxyethyl)-3-(3,4-dichlorophenyl)piperidine

HRID 742629Notes

Reaction equation

HRID 742629 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]1([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[CH2:15][NH:14][C:13](=O)[CH2:12][CH2:11]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]1([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[CH2:11][CH2:12][CH2:13][NH:14][CH2:15]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 109596635-(2-Tetrahydropyranyloxyethyl)-5-(3,4-dichlorophenyl)piperidinoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 211976913-(2-Tetrahydropyranyloxyethyl)-3-(3,4-dichlorophenyl)piperidineYield 90.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

3.9 g of the 5-(2-tetrahydropyranyloxyethyl)-5-(3,4-dichlorophenyl)piperidinone prepared above are dissolved in 50 ml of tetrahydrofuran and the solution is added to a suspension of 0.9 g of lithium aluminum hydride in 5 ml of THF heated to 60° C. The reaction mixture is heated for one hour at 60° C. and then cooled. 1 ml of water, 1 ml of 4N sodium hydroxide and 3 ml of water are added. The insoluble portion is filtered off and the filtrate is concentrated under vacuum. The residue is taken up in ethyl ether, dried over MgSO4 and concentrated under vacuum to give 3.4 g of the expected product.

Workup

  1. temperatureThe reaction mixture is heated for one hour at 60° C.
  2. temperaturecooled
  3. filtrationThe insoluble portion is filtered off
  4. concentrationthe filtrate is concentrated under vacuum
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5d415b49404f47b483d655b726ebda40
Source dataset
uspto-grants-1996_09
Patent number
US05554763

Reaction notes

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