1,3-Dimethoxybenzene → HCID 13180314, compound

HRID 867013Notes

Reaction equation

HRID 867013 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].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25]C)[CH:20]=1>>[C:1]([N:4]1[CH2:12][CH2:11][CH:7]([C:8](=[O:9])[C:22]2[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][C:21]=2[OH:25])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

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

Product 1

HCID 13180314HCID 13180314, compound

Procedure

16.5 g of 1-acetylisonipecotoyl chloride, Example 1(b) are slowly added to a stirring mixture of 60 ml of m-dimethoxybenzene and 20.0 g of aluminum chloride. Stirring is continued for 1 hour at ambient temperature and then for an additional 1 hour at about 100° C. The reaction mixture is allowed to cool to ambient temperature, 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 hexane to effect a white solid which is collected and dried. Recrystallization from ethyl acetate yields colorless needles, mp 138°-140° C., 1-acetyl-4-(2-hydroxy-4-methoxybenzoyl)piperidine.

Workup

  1. waitfor an additional 1 hour at about 100° C
  2. extractionextracted with chloroform
  3. customThe combined extracts are dried
  4. customthe chloroform is removed
  5. customleaving a yellow oil
  6. customThe oil is triturated with hexane
  7. customis collected
  8. customdried
  9. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-08bcd96c96ad4562a88d62565086a7e8
Source dataset
uspto-grants-1978_07
Patent number
US04101663

Reaction notes

Loading…