Sodium hydride → HCID 59833652, compound

HRID 270044Notes

Reaction equation

HRID 270044 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][C:13]([CH2:24][OH:25])([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2F)[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CCCCCCC.O1CCCC1>[CH2:3]([N:10]1[CH2:15][CH2:14][C:13]2([CH2:16][C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:25][CH2:24]2)[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 68961767[1-Benzyl-4-(2-fluorobenzyl)piperidin-4-yl)methanol

Product 1

HCID 59833652HCID 59833652, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8900HeptaneSolvent

Procedure

Sodium hydride (350 mg, 7.0 mmol, 50% disp in oil) was washed three times with heptane, under nitrogen atmosphere, and then dissolved in tetrahydrofuran (50 mL). A solution of [1-benzyl-4-(2-fluorobenzyl)piperidin-4-yl)methanol (1 g, 3.2 mmol) in tetrahydrofuran (30 mL) was added and the resulting mixture was refluxed for 3 hrs. The cooled solution was partitioned between water and ethyl acetate and the organic layer was dried over magnesium sulphate and concentrated. The crude product was purified on silica (dichloromethane/methanol) to give 0.83 g (89%) of the subtitle compound.

Workup

  1. temperaturethe resulting mixture was refluxed for 3 hrs
  2. customThe cooled solution was partitioned between water and ethyl acetate
  3. dry with materialthe organic layer was dried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe crude product was purified on silica (dichloromethane/methanol)

Sources & evidence

ORD record
ord-60bdd320967742c2853f7147e773af0d
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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