Toluene → 1-Benzyl-4-hydroxy-4-(1,4-benzodioxan-5-yl)piperidine

HRID 963257

Reaction equation

HRID 963257 reaction equation
C1(C)C=CC=CC=1.Br[C:9]1[C:18]2[O:17][CH2:16][CH2:15][O:14][C:13]=2[CH:12]=[CH:11][CH:10]=1.C([Li])CCC.[CH2:24]([N:31]1[CH2:36][CH2:35][C:34](=[O:37])[CH2:33][CH2:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O>[CH2:24]([N:31]1[CH2:36][CH2:35][C:34]([OH:37])([C:9]2[C:18]3[O:17][CH2:16][CH2:15][O:14][C:13]=3[CH:12]=[CH:11][CH:10]=2)[CH2:33][CH2:32]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 192201-Benzyl-4-piperidoneHCID 187872685-Bromo-2,3-dihydro-1,4-benzodioxineHCID 178418339Butyllithium

Product 1

HCID 190820021-Benzyl-4-hydroxy-4-(1,4-benzodioxan-5-yl)piperidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A toluene solution (10 ml) of 5-bromo-2,3-dihydrobenzo[1,4]dioxin (10 mmol) was stirred under argon at 0° C. and was treated with the dropwise addition of n-butyllithium (10 mmol) over ten minutes. After stirring for a further twenty minutes a solution of 1-benzyl-4-piperidone in toluene (10 mmol in 10 ml) was added dropwise over five minutes. Stirring was continued for two hours, at which point water (100 ml) was added and the product extracted into ethyl acetate (4×50 ml). The combined organics were washed with water (2×50 ml), brine (75 ml) and dried (MgSO4). Filtration and concentration in vacuo gave an oil.

Workup

  1. additionwas added dropwise over five minutes
  2. additionwas added
  3. extractionthe product extracted into ethyl acetate (4×50 ml)
  4. washThe combined organics were washed with water (2×50 ml), brine (75 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and concentration in vacuo
  7. customgave an oil

Sources & evidence

ORD record
ord-3739f71d30514f818eec72796ec5874e
Source dataset
uspto-grants-1998_06
Patent number
US05763460

Linked notes

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