Potassium Iodide → 4-[Bis(4-methoxyphenyl)methyl]-1-[3-(3,4-dimethoxyphenoxy)propyl]piperidine

HRID 1193676Notes

Reaction equation

HRID 1193676 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]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[CH:30]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(O)CCC>[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]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[CH:30]=3)[CH2:12][CH2:11]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 132105144-(3-Chloropropoxy)-1,2-dimethoxybenzeneHCID 144071674-[Bis(4-methoxyphenyl)methyl]piperidine

Product 1

HCID 144070954-[Bis(4-methoxyphenyl)methyl]-1-[3-(3,4-dimethoxyphenoxy)propyl]piperidine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 5.58 g (0.02 mole) of 4-[bis(4-methoxyphenyl)methyl]piperidine, 4.83 g (0.021 mole) of 4-(3-chloropropoxy)-1,2-dimethoxybenzene, and potassium carbonate, 5.52 g (0.04 mole) was heated overnight at reflux in 350 ml of 1-butanol containing potassium iodide (0.3 g). The reaction mixture was stripped to dryness, and the residue partitioned between chloroform-5% sodium hydroxide and chloroform-water. Removal of chloroform gave a dark brown oil. The oil was subjected to column chromatography on a silica gel column with elution via ethyl acetate-dimethoxy ethane. This produced 4.72 g (46.7%) of dark brown oil.

Workup

  1. temperaturewas heated overnight
  2. customthe residue partitioned between chloroform-5% sodium hydroxide and chloroform-water
  3. customRemoval of chloroform
  4. customgave a dark brown oil
  5. washThe oil was subjected to column chromatography on a silica gel column with elution via ethyl acetate-dimethoxy ethane

Sources & evidence

ORD record
ord-ef17b701f72a4e149f3c2f684f467830
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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