1-Butanol → HCID 23036390, compound

HRID 1709923Notes

Reaction equation

HRID 1709923 reaction equation
Cl.[F:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[CH:10]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1[F:24])[CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.Cl[CH2:26][CH2:27][CH2:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([C:36](=[O:38])[CH3:37])=[CH:32][C:31]=1[O:39][CH3:40].[C:41](=[O:44])([O-:43])[O-].[K+].[K+].[I-].[K+].C([OH:53])CCC>CO.C(OCC)C>[C:40]([OH:39])(=[O:53])[C:41]([OH:43])=[O:44].[F:24][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[CH:10]([C:4]1[CH:5]=[CH:6][C:7]([F:9])=[CH:8][C:3]=1[F:2])[CH:11]1[CH2:12][CH2:13][N:14]([CH2:26][CH2:27][CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([C:36](=[O:38])[CH3:37])=[CH:32][C:31]=2[O:39][CH3:40])[CH2:15][CH2:16]1

Participants

7

Reactant 5

HCID 2631-ButanolHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenoneHCID 19983090HCID 19983090, compound

Product 1

HCID 23036390HCID 23036390, compound

Reagents, catalysts & solvents 1

HCID 21864698Diethyl ether methanolSolvent

Procedure

A mixture of the free base of 4-[bis(2,4-difluorophenyl)methyl]piperidine hydrochloride [1:1 (7.30 g, 0.023 mole), 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (5.57 g, 0.023 mole), and potassium carbonate (5.54 g, 0.04 mole) was heated overnight at reflux in 350 ml of 1-butanol containing potassium iodide (0.2 g). The reaction mixture was filtered and then concentrated to dryness. The residue was dissolved in chloroform, and the solution was extracted with 5% sodium hydroxide. The chloroform layer was dried over sodium sulfate and filtered. The removal of chloroform provided a dark brown oil (quantitative). This material was converted to the oxalate salt in methanol-ethyl ether. A white solid was isolated and dried in vacuo overnight at 80° C. This procedure furnished 8.23 g (57.7%) of white, crystalline product, mp 151°-153° C.

Workup

  1. temperaturewas heated overnight
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated to dryness
  4. dissolutionThe residue was dissolved in chloroform
  5. extractionthe solution was extracted with 5% sodium hydroxide
  6. dry with materialThe chloroform layer was dried over sodium sulfate
  7. filtrationfiltered
  8. customThe removal of chloroform
  9. customprovided a dark brown oil (quantitative)
  10. customA white solid was isolated
  11. customdried in vacuo overnight at 80° C
  12. customThis procedure furnished 8.23 g (57.7%) of white, crystalline product, mp 151°-153° C.

Sources & evidence

ORD record
ord-0615b9041733479eb5a9332e4463d608
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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