1,3-Dimethoxybenzene → HCID 13180315, compound

HRID 867014Notes

Reaction equation

HRID 867014 reaction equation
[C:1]([N:4]1[CH2:12][CH2:11][CH:7]([C:8](Cl)=[O:9])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[C:1]([N:4]1[CH2:12][CH2:11][CH:7]([C:8](=[O:9])[C:18]2[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[CH:16][C:17]=2[O:21][CH3:22])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 90251,3-DimethoxybenzeneHCID 1009501-Acetylpiperidine-4-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13180315HCID 13180315, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

18.7 g of 1-acetylisonipecotoyl chloride, Example 1(b) are added slowly to a stirred mixture of 40.0 g of m-dimethoxybenzene and 19.2 g of aluminum chloride in 75 ml of carbon disulfide. The reaction mixture is stirred at ambient temperature for an hour, poured into ice-water and extracted with chloroform, the combined extracts are dried and the chloroform is removed, leaving a yellow oil. The oil is triturated with ether to give a white solid, which is recrystallized twice from ethyl acetate to give the pure solid, mp 132°-134° C., 1-acetyl-4-(2,4-dimethoxybenzoyl)piperidine.

Workup

  1. extractionextracted with chloroform
  2. customthe combined extracts are dried
  3. customthe chloroform is removed
  4. customleaving a yellow oil
  5. customThe oil is triturated with ether
  6. customto give a white solid, which
  7. customis recrystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-66ef901be1644657bc6df7eab1082a4d
Source dataset
uspto-grants-1978_07
Patent number
US04101663

Reaction notes

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