Diethyl Ether → HCID 22645406, compound

HRID 2414268Notes

Reaction equation

HRID 2414268 reaction equation
[CH2:1]([N:7]1[CH2:12][CH2:11][C:10]([CH3:21])([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]#[N:20])[CH:14]=2)[CH:9]([CH3:22])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[OH-].[Na+]>O1CCCC1.O>[CH2:1]([N:7]1[CH2:12][CH2:11][C:10]([CH3:21])([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][NH2:20])[CH:14]=2)[CH:9]([CH3:22])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22645388HCID 22645388, compound

Product 1

HCID 22645406HCID 22645406, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-hexyl-3,4-dimethyl-4-(3-cyanophenyl)piperidine (Example 1, 800 mg, 2.68 mmol) in anhydrous tetrahydrofuran (40 mL) at 0° C. under nitrogen was added lithium aluminium hydride (1.0 M in tetrahydrofuran, 4.0 mL, 4.0 mmol). The reaction mixture was allowed to warm to room temperature, before being heated to 37° C. for 30 minutes. Subsequently, diethyl ether (50 mL), then aqueous sodium hydroxide (0.3 mL, 15% w/v solution) and finally water (0.45 mL) were added. The white solid formed was filtered off. The filtrate was washed with saturated aqueous sodium hydrogencarbonate solution (2×50 mL). The aqueous phases were back-extracted with diethyl ether (50 mL). The combined organics were dried (MgSO4) and concentrated in vacuo to give the title compound as an oil (770 mg).

Workup

  1. temperaturebefore being heated to 37° C. for 30 minutes
  2. customThe white solid formed
  3. filtrationwas filtered off
  4. washThe filtrate was washed with saturated aqueous sodium hydrogencarbonate solution (2×50 mL)
  5. extractionThe aqueous phases were back-extracted with diethyl ether (50 mL)
  6. dry with materialThe combined organics were dried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-92ced4b309a647188f8e357f478e2c6d
Source dataset
uspto-grants-2004_11
Patent number
US06812236B2

Reaction notes

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