Potassium Iodide → 1-[4-[3-[4-[Bis(4-methoxyphenyl)methyl]-1-piperidinyl]propoxy]-3-methoxyphenyl]ethanone oxalate

HRID 1193696Notes

Reaction equation

HRID 1193696 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:5][CH:4]=1.Cl[CH2:25][CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35](=[O:37])[CH3:36])=[CH:31][C:30]=1[O:38][CH3:39].[C:40](=[O:43])([O-:42])[O-].[K+].[K+].[I-].[K+]>C(O)CCC>[C:23]([OH:22])(=[O:28])[C:40]([OH:42])=[O:43].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[CH:10]2[CH2:15][CH2:14][N:13]([CH2:25][CH2:26][CH2:27][O:28][C:29]3[CH:34]=[CH:33][C:32]([C:35](=[O:37])[CH3:36])=[CH:31][C:30]=3[O:38][CH3:39])[CH2:12][CH2:11]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenoneHCID 144071674-[Bis(4-methoxyphenyl)methyl]piperidine

Product 1

HCID 212722481-[4-[3-[4-[Bis(4-methoxyphenyl)methyl]-1-piperidinyl]propoxy]-3-methoxyphenyl]ethanone oxalateYield 54.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 7.78 g (0.025 mole) of 4-[bis(4-methoxyphenyl)methyl]piperidine, 6.05 g (0.025 mole) of 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone, and potassium carbonate (5.53 g, 0.04 mole) in 300 ml of 1-butanol containing potassium iodide (0.3 g) was refluxed overnight. The reaction mixture was stripped to dryness and the residue was partitioned between chloroform and water; removal of chloroform in vacuo gave a dark brown oil. The oil was subjected to column chromatography on silica gel using a gradient elution composed of methanol and ethyl acetate. The corresponding fractions from the column were combined and reacted with oxalic acid. Recrystallization of the salt from methanol-diethyl ether gave 4.16 g (27.4%) of white solid, m.p. 163.5°-165° C.

Workup

  1. temperaturewas refluxed overnight
  2. customthe residue was partitioned between chloroform and water
  3. customremoval of chloroform in vacuo
  4. customgave a dark brown oil
  5. washa gradient elution
  6. customreacted with oxalic acid
  7. customRecrystallization of the salt from methanol-diethyl ether

Sources & evidence

ORD record
ord-ac4239a4c64142ef8051c125327b523f
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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