1-Butanol → 4-[Bis(4-fluorophenyl)methyl]-1-[3-(3,4-dimethoxyphenoxy)propyl]piperidine oxalate

HRID 1193674Notes

Reaction equation

HRID 1193674 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.Cl[CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=1.[C:37](=[O:40])([O-:39])[O-].[K+].[K+].[I-].[K+].C([OH:49])CCC>>[C:36]([OH:35])(=[O:49])[C:37]([OH:39])=[O:40].[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:9]2[CH2:14][CH2:13][N:12]([CH2:23][CH2:24][CH2:25][O:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=3)[CH2:11][CH2:10]2)=[CH:20][CH:19]=1

Participants

6

Reactant 5

HCID 2631-ButanolHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 132105144-(3-Chloropropoxy)-1,2-dimethoxybenzeneHCID 132505444-[Bis(4-fluorophenyl)methyl]piperidine

Product 1

HCID 230363874-[Bis(4-fluorophenyl)methyl]-1-[3-(3,4-dimethoxyphenoxy)propyl]piperidine oxalate

Procedure

A mixture of 6.02 g (0.021 mole) of 4-[bis(4-fluorophenyl)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 refluxed overnight in 300 ml of 1-butanol containing potassium iodide (0.3 g). The reaction mixture was stripped to dryness and partitioned between chloroform and water several times. The chloroform layer was dried over anhydrous sodium sulfate and then filtered. The chloroform was removed by rotary evaporator. The oil obtained was converted to the oxalate salt and then recrystallized from methanol-diethyl ether and methanol isopropanol ether. This furnished 7.77 g (64.7%) of white solid; m.p. 188° C.

Workup

  1. custompartitioned between chloroform and water several times
  2. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customThe chloroform was removed by rotary evaporator
  5. customThe oil obtained
  6. customrecrystallized from methanol-diethyl ether and methanol isopropanol ether

Sources & evidence

ORD record
ord-2e5349f9ee524b78a66a44239b5d3db7
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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