1-Butanol → HCID 23036362, compound

HRID 1193669Notes

Reaction equation

HRID 1193669 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.Br[CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:32](=[O:35])([O-:34])[O-].[Na+].[Na+].C([OH:42])CCC>>[C:26]([OH:25])(=[O:42])[C:32]([OH:34])=[O:35].[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][O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:11][CH2:10]2)=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 2631-ButanolHCID 10340Sodium CarbonateHCID 68526Benzene, (2-bromoethoxy)-HCID 132505444-[Bis(4-fluorophenyl)methyl]piperidine

Product 1

HCID 23036362HCID 23036362, compoundYield 60.3%

Procedure

A mixture, 5.83 g (0.02 mole) of 4-[bis(4-fluorophenyl)methyl]piperidine 4.02 g (0.02 mole) of (2-bromoethoxy)benzene and sodium carbonate (3.18 g, 0.03 mole) was heated overnight at gentle reflux in 300 ml of 1-butanol. The reaction was filtered and solvent removed in vacuo. The residue was dissolved in chloroform and extracted with water and 5% sodium hydroxide. Removal of chloroform gave an oil which was converted to the oxalate salt. The salt was recrystallized from methanol-diethyl ether to give 6.0 g (60.3%) of white crystalline product, m.p. 180°-182° C.

Workup

  1. filtrationThe reaction was filtered
  2. customsolvent removed in vacuo
  3. dissolutionThe residue was dissolved in chloroform
  4. extractionextracted with water and 5% sodium hydroxide
  5. customRemoval of chloroform
  6. customgave an oil which
  7. customThe salt was recrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-44e920e6b0a44b27a4a3d1de3abe41fb
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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