Anisole → HCID 18621545, compound

HRID 324549Notes

Reaction equation

HRID 324549 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)(=O)[CH3:2].[Cl-].[Cl-].[Cl-].[Al+3].[C:24]1([O:30]C)C=CC=CC=1.C(N1CCC(C(Cl)=O)CC1)(=O)C>C(=S)=S>[OH:30][CH2:24][CH2:2][CH2:1][N:4]1[CH2:9][CH2:8][CH:7]([C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 7519AnisoleHCID 1009501-Acetylpiperidine-4-carbonyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 186215481-[4-(4-Methoxybenzoyl)piperidin-1-yl]ethan-1-one

Product 1

HCID 18621545HCID 18621545, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

1-Acetyl-4-(4-methoxybenzoyl)piperidine. To a suspension of aluminum trichloride (3.40 g, 25.7 mmol) in CS2 (15 mL) were added anisole (1.90 mL, 17.6 mmol) and, portionwise, N-acetylisonipecotoyl chloride (2.40 g, 11.7 mmol). After the addition was complete, the mixture was refluxed for 1 h. The solvent was decanted and the red residue was dissolved in 5% HCl (50 mL) and was extracted with EtOAc (4×30 mL). The combined organic phase was dried and was concentrated under reduced pressure to afford the title compound as a colorless solid (1.8 g, 60%):mp 102-105° C.; 1H NMR (CDCl3) d 1.50-1.75 (m, 1H), 1.70-2.00 (m, 3H), 2.10 (s, 3H), 2.70-2.90 (m, 1H), 3.15-3.30 (m, 1H), 3.40-3.53 (m, 1H), 3.86 (s, 3H), 3.85-4.00 (m, 1H), 4.56 (d, J=13.2 Hz, 1H), 6.94 (d, J=8.7 Hz, 2H), 7.92 (d, J=9.0 Hz, 2H).

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed for 1 h
  3. customThe solvent was decanted
  4. dissolutionthe red residue was dissolved in 5% HCl (50 mL)
  5. extractionwas extracted with EtOAc (4×30 mL)
  6. customThe combined organic phase was dried
  7. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-f3ae503054e44f3688453de28af08b7b
Source dataset
uspto-grants-2001_04
Patent number
US06218404B1

Reaction notes

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