Diethyl Ether → HCID 58111159, compound

HRID 222581Notes

Reaction equation

HRID 222581 reaction equation
[F:1][C:2]([CH3:30])([CH3:29])[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH2:20][CH2:21][N:22]([S:25]([CH3:28])(=[O:27])=[O:26])[CH2:23][CH:24]=3)=[CH:15][CH:14]=2)[CH2:7][CH2:6]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].C(OCC)C>O1CCCC1>[F:1][C:2]([CH3:30])([CH3:29])[CH2:3][N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH2:24][CH2:23][N:22]([S:25]([CH3:28])(=[O:27])=[O:26])[CH2:21][CH:20]=3)=[CH:15][CH:14]=2)[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 668651311-Propanone, 2-fluoro-2-methyl-1-[4-[[4-[1,2,3,6-tetrahydro-1-(methylsulfonyl)-4-pyridinyl]phenoxy]methyl]-1-piperidinyl]-

Product 1

HCID 58111159HCID 58111159, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-fluoro-1-{4-[4-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenoxymethyl]-piperidin-1-yl}-2-methyl-propan-1-one (1.00 g, 2.28 mmol) in tetrahydrofuran (23 mL) at rt is added via cannula a 1 M solution of lithium aluminum hydride in tetrahydrofuran (7.18 g, 7.98 mL, 7.98 mmol). After 1 h, sodium sulfate decahydrate is added carefully. The mixture is stirred for 15 min and the solid is filtered off and washed with dichloromethane. The solvent is removed and the residue is purified via silica gel chromatography, eluting with dichloromethane:ethyl acetate 5.6:1 to 2:1 to obtain a solid. Diethyl ether is added and the solid is filtered and washed with diethyl ether and ethyl acetate to obtain 0.245 g of the title compound as a white solid. MS (m/z) 425 (M+1).

Workup

  1. filtrationthe solid is filtered off
  2. washwashed with dichloromethane
  3. customThe solvent is removed
  4. customthe residue is purified via silica gel chromatography
  5. washeluting with dichloromethane:ethyl acetate 5.6:1 to 2:1
  6. customto obtain a solid
  7. filtrationthe solid is filtered
  8. washwashed with diethyl ether and ethyl acetate

Sources & evidence

ORD record
ord-d5a344eda28a4f3398a6be2e90db5f42
Source dataset
uspto-grants-2012_06
Patent number
US08207344B2

Reaction notes

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