Bromobenzene → HCID 57686303, compound

HRID 238261Notes

Reaction equation

HRID 238261 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:15])(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Cl-].[Cl-].[Al+3].[OH-].[Na+].[Br:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:26]2[CH:27]=[CH:28][C:23]([Br:22])=[CH:24][CH:25]=2)([CH3:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 7961BromobenzeneHCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 108459131-Benzyl-4-methylpiperidin-4-ol

Product 1

HCID 57686303HCID 57686303, compound

Conditions

Temperature
100 °C

Procedure

To a solution of 1-benzyl-4-methyl-piperidin-4-ol (0.4 g, 1.95 mmol) in bromobenzene (1.2 mL) was added aluminium trichloride (0.39 g, 2.9 mmol). The mixture was then heated to 100° C. for 14 hours and left standing at room temperature for 48 hours. Aqueous sodium hydroxide (1 N, 30 mL) was added and the products extracted into ethyl acetate, dried over magnesium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by flash chromatography on silica eluting with 0-25% ethyl acetate/hexane. The fractions containing the desired product were concentrated under vacuum to give the title compound as a brown oil (0.5 g). LCMS m/z 344.5 [M+H]+. R.T.=3.13 min (Analytical Method 4).

Workup

  1. waitleft
  2. extractionthe products extracted into ethyl acetate
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent removed by evaporation under vacuum
  6. customThe residue was purified by flash chromatography on silica eluting with 0-25% ethyl acetate/hexane
  7. additionThe fractions containing the desired product
  8. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-a8ab2757a0024c21a9e4b7f76e8d0262
Source dataset
uspto-grants-2014_02
Patent number
US08642621B2

Reaction notes

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