1-Butanol → HCID 21272255, compound

HRID 1193671Notes

Reaction equation

HRID 1193671 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][CH:30]=[CH:29][C:28]=1[F:33].[C:34](=[O:37])([O-:36])[O-].[Na+].[Na+].[I-].[K+].C([OH:46])CCC>>[C:27]([OH:26])(=[O:46])[C:34]([OH:36])=[O:37].[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][CH:30]=[CH:29][C:28]=3[F:33])[CH2:11][CH2:10]2)=[CH:20][CH:19]=1

Participants

6

Reactant 5

HCID 2631-ButanolHCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 30182221-(3-Chloropropoxy)-2-fluorobenzeneHCID 132505444-[Bis(4-fluorophenyl)methyl]piperidine

Product 1

HCID 21272255HCID 21272255, compoundYield 271.5%

Procedure

A mixture of 5.85 g (0.02 mole) of 4-[bis(4-fluorophenyl)methyl]piperidine, 3.76 g (0.02 mole) of 2-(3-chloropropoxy)-1-fluorobenzene, and sodium carbonate (4.80 g, 0.045 mole) in 300 ml of 1-butanol containing 0.3 g of potassium iodide was heated overnight at gentle reflux. The reaction mixture was stripped to dryness and the resulting oil partitioned between chloroform-5% sodium hydroxide and then between chloroform-water. Removal of chloroform gave an oil which was converted to the oxalate salt. The salt was recrystallized from methanol-diethyl ether. The salt was subsequently triturated with isopropanol, and was dried overnight at 80° C. to give 5.82 g (55%) of product, m.p. 182°-183° C.

Workup

  1. temperaturewas heated overnight at gentle reflux
  2. customthe resulting oil partitioned between chloroform-5% sodium hydroxide
  3. customRemoval of chloroform
  4. customgave an oil which
  5. customThe salt was recrystallized from methanol-diethyl ether
  6. customThe salt was subsequently triturated with isopropanol
  7. customwas dried overnight at 80° C.

Sources & evidence

ORD record
ord-ba241585e812414ab9c27a364fa62625
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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