Chlorobenzene → HCID 23136891, compound

HRID 917156Notes

Reaction equation

HRID 917156 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.[Al+3].[Cl-].[Cl-].[Cl-].[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[Cl:20])([CH3:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7964ChlorobenzeneHCID 6451240Aluminum(III) ChlorideHCID 108459131-Benzyl-4-methylpiperidin-4-ol

Product 1

HCID 23136891HCID 23136891, compoundYield 10%

Procedure

A solution of 1-Benzyl-4-methyl-piperidin-4-ol (4.5 g, 22 mmol) in chlorobenzene (60 mL) was treated with anhydrous AlCl3 (15 g, 110 mmol). This mixture was stirred for 3 hr at reflux, then quenched into ice (250 g), basified with sodium hydroxide, and extracted with ethyl acetate (3×100 mL). The combined organics were dried over sodium sulfate and evaporated in vacuo. The residue was purified by silica gel chromatography (CH2Cl2→90:10 CH2Cl2/methanol) to yield 0.59 g (10%) of the title compound, ESI-MS m/z: 300 [M+1].

Workup

  1. temperatureat reflux
  2. customquenched into ice (250 g)
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel chromatography (CH2Cl2→90:10 CH2Cl2/methanol)

Sources & evidence

ORD record
ord-8bb396f89b204bbfa3cb1a143f4ed786
Source dataset
uspto-grants-2007_09
Patent number
US07271176B2

Reaction notes

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