Potassium Iodide → 1-[4,4-Bis(4-fluorophenyl)butyl]-3,4,4-trimethoxypiperidine

HRID 345552Notes

Reaction equation

HRID 345552 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH:5]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.CO[CH:22]1[CH:27]([O:28][CH3:29])[CH:26]([O:30][CH3:31])[CH2:25][NH:24][CH2:23]1.[C:32](=O)([O-])[O-:33].[Na+].[Na+].[I-].[K+]>CC(C)CC(=O)C>[F:12][C:9]1[CH:10]=[CH:11][C:6]([CH:5]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:4][CH2:3][CH2:2][N:24]2[CH2:23][CH2:22][C:27]([O:28][CH3:29])([O:33][CH3:32])[CH:26]([O:30][CH3:31])[CH2:25]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 199923503,4,5-Trimethoxypiperidine

Product 1

HCID 198834801-[4,4-Bis(4-fluorophenyl)butyl]-3,4,4-trimethoxypiperidine

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 56.2 parts of 1,1'-(4-chlorobutylidene) bis[4-fluorobenzene], 31.5 parts of 3,4,5-trimethoxypiperidine, 42.5 parts of sodium carbonate, 1 part of potassium iodide and 960 parts of 4-methyl-2-pentanone was stirred and refluxed for 18 hours. The reaction mixture was cooled, filtered and the filtrate was evaporated, yielding 82.5 parts of 1-[4,4-bis(4-fluorophenyl)butyl]-3,4,4-trimethoxypiperidine as a residue (intermediate 66).

Workup

  1. temperaturerefluxed for 18 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-da97066c0a4a4434981027ec2ab63d97
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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