Veratrole → HCID 71227331, compound

HRID 713447Notes

Reaction equation

HRID 713447 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14].[C:15]([N:18]1[CH2:23][CH2:22][CH:21]([C:24](Cl)=[O:25])[CH2:20][CH2:19]1)(=[O:17])[CH3:16]>CCCCC>[CH3:5][O:6][C:7]1[CH:12]=[C:11]([CH:10]=[CH:9][C:8]=1[O:13][CH3:14])[C:24]([CH:21]1[CH2:20][CH2:19][N:18]([C:15](=[O:17])[CH3:16])[CH2:23][CH2:22]1)=[O:25]

Participants

5

Reactant 3

HCID 7043VeratroleHCID 1009501-Acetylpiperidine-4-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 71227331HCID 71227331, compound

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Conditions

Temperature
100 °C

Procedure

To a rapidly stirred slurry of aluminum chloride (1.1 g, 8.2 mmol) and 1,2-dimethoxybenzene (3.5 mL) at ambient temperature was added 1-acetylpiperidine-4-carbonyl chloride (0.8 g, 4.2 mmol). The reaction mixture was heated at reflux (100° C.) for 1.5 hours and then poured into 30 mL of ice water, the mixture was extracted with DCM (50 mL) and the organic layer was washed with water and dried over Na2SO4. The solvent was removed in vacuo to give an oil. Trituration of the oil with pentane gave the title product (0.88 g, 2.87 mmol) as a white solid. MS (ESI) m/z 292.4 (M+H+); HPLC (Novapak 150×3.9 mm C-18 column: mobile phase: 35-90% acetonitrile/water with 0.1% TFA, at 2 mL/min over 2 min.) t 0.86 min.

Workup

  1. temperatureThe reaction mixture was heated
  2. extractionthe mixture was extracted with DCM (50 mL)
  3. washthe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo
  6. customto give an oil

Sources & evidence

ORD record
ord-d77c08130a6d47a7b6b51971d05aeb78
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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