Water → HCID 11977495, compound

HRID 657639Notes

Reaction equation

HRID 657639 reaction equation
[N:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][N:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[N:1]1([CH2:7][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][N:25]4[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]4)=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23150261HCID 23150261, compound

Product 1

HCID 11977495HCID 11977495, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(3-{[4′-(piperidinocarbonyl)biphenyl-4-yl]oxy}propyl)-piperidine (500 mg) in tetrahydrofuran (20 mL) is added lithium aluminium hydride (105 mg). The suspension is stirred at room temperature for three hours, then hydrolysed through the successive addition of water (110 μL), 15% aqueous solution of sodium hydroxide (110 μL) and water (330 μL). The mixture is stirred for an half hour and filtrated. The filtrate is dried over magnesium sulfate and concentrated under reduced pressure. The product thus obtained is recrystallized in diisopropyl oxide and purified by chromatography over silica gel with a gradient dichloromethane/methanol from 98/2 to 85/15. Fraction containing the expected product are pooled, concentrated under reduced pressure to give 125 mg of 1-(3-{[4′-(piperidinomethyl)biphenyl-4-yl]oxy}propyl)piperidine as white crystals melting at 90° C.

Workup

  1. stirringThe mixture is stirred for an half hour
  2. filtrationfiltrated
  3. dry with materialThe filtrate is dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe product thus obtained
  6. customis recrystallized in diisopropyl oxide
  7. custompurified by chromatography over silica gel with a gradient dichloromethane/methanol from 98/2 to 85/15
  8. additionFraction containing the expected product
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f406084385d74055bf20049b65630b7e
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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