Potassium Iodide → 1-[4-[3-[4-[2,2-Bis(4-fluorophenyl)-2-hydroxyethyl]-1-piperidinyl]propoxy]-3-methoxyphenyl]ethanone fumarate hydrate

HRID 1709912Notes

Reaction equation

HRID 1709912 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)([OH:16])[CH2:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[C:24]([C:27]1[CH:37]=[CH:36][C:30]([O:31][CH2:32][CH2:33][CH2:34]Cl)=[C:29]([O:38][CH3:39])[CH:28]=1)(=[O:26])[CH3:25].[C:40](=[O:43])([OH:42])[O-].[Na+].[I-].[K+]>C(O)CCC>[OH2:16].[C:8]([OH:26])(=[O:16])/[CH:17]=[CH:22]/[C:40]([OH:42])=[O:43].[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)([OH:16])[CH2:9][CH:10]2[CH2:11][CH2:12][N:13]([CH2:34][CH2:33][CH2:32][O:31][C:30]3[CH:36]=[CH:37][C:27]([C:24](=[O:26])[CH3:25])=[CH:28][C:29]=3[O:38][CH3:39])[CH2:14][CH2:15]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenoneHCID 13754513alpha,alpha-Bis(4-fluorophenyl)-4-piperidineethanol

Product 1

HCID 230363741-[4-[3-[4-[2,2-Bis(4-fluorophenyl)-2-hydroxyethyl]-1-piperidinyl]propoxy]-3-methoxyphenyl]ethanone fumarate hydrate

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 4.52 g (0.0143 mole) of α,α-bis(4-fluorophenyl)-4-piperidineethanol, 3.75 g (0.0155 mole) of 3-(4-acetyl-2-methoxyphenoxy)-1-chloropropane, 4.1 g (0.049 mole) of sodium bicarbonate, and 0.20 g (0.0012 mole) of potassium iodide in 300 ml of 1-butanol was heated at reflux for 8 hr. The solvent was removed in vacuo, and the residue was partitioned between methylene chloride and dilute sodium hydroxide. The methylene chloride solution was treated with a small portion of activated charcoal and was dried over magnesium sulfate. The solvent was removed in vacuo to give the non-salt form of the title compound. This was converted to the fumarate salt and the salt was crystallized from methanol/ether to give 5.94 g (64.9%) of the title compound as a white, crystalline solid, mp 135°-136° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 hr
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between methylene chloride and dilute sodium hydroxide
  5. additionThe methylene chloride solution was treated with a small portion of activated charcoal
  6. dry with materialwas dried over magnesium sulfate
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e27b3a1717ed4723bb3854b3e65ff8ab
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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