Water → HCID 19823695, compound

HRID 728299Notes

Reaction equation

HRID 728299 reaction equation
[CH3:1][N:2]([CH:4]([C:9]1([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1)[CH2:5][CH2:6]OC)[CH3:3].[H-].[Na+].[CH:22]([C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)=[CH2:23].O.[O:31]1CCC[CH2:32]1>CCOCC>[CH3:3][N:2]([CH:4]([C:9]1([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[CH2:10][CH2:11][CH2:12]1)[CH2:5][CH2:6][CH2:32][O:31][CH2:23][CH2:22][C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)[CH3:1]

Participants

7

Reactant 5

HCID 962WaterHCID 75024-VinylpyridineHCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 19823628HCID 19823628, compound

Product 1

HCID 19823695HCID 19823695, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 3-[1-(4-chlorophenyl)cyclobutyl]-3-dimethylaminopropan-1-ol (3 g prepared as described in Example 211) in tetrahydrofuran (50 ml) was added to a stirred suspension of sodium hydride (1.02 g of a 50% dispersion in mineral oil) in tetrahydrofuran (60 ml). The mixture was stirred at ambient temperature for one hour and a solution of 4-vinylpyridine (5.74 ml) in tetrahydrofuran (10 ml) was added and the mixture allowed to stand for 72 hours at ambient temperature and then heated under reflux for 48 hours. Water was added dropwise to the cooled reaction mixture which was then extracted with ether. The extracts were washed, dried and evaporated to give an oil which was dissolved in ether, filtered and the filtrate evaporated. The residue was heated at 95° C./0.5 mm Hg for 2 hours and then purified by flash chromatography on a silica column using a 9:1 mixture of light petroleum (b.p. 60°-80° C.) and propan- 2-ol as eluant followed by high performance liquid chromatography. The product was heated at 80° C./20 mm Hg for 5 hours to leave N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-4-[2-(4-pyridyl)ethoxy]butylamine as an oil the boiling point of which was not determined.

Workup

  1. waitto stand for 72 hours at ambient temperature
  2. temperatureheated
  3. temperatureunder reflux for 48 hours
  4. extractionwas then extracted with ether
  5. washThe extracts were washed
  6. customdried
  7. customevaporated
  8. customto give an oil which
  9. filtrationfiltered
  10. customthe filtrate evaporated
  11. temperatureThe residue was heated at 95° C./0.5 mm Hg for 2 hours
  12. custompurified by flash chromatography on a silica column
  13. additiona 9:1 mixture of light petroleum (b.p. 60°-80° C.) and propan- 2-ol as eluant
  14. temperatureThe product was heated at 80° C./20 mm Hg for 5 hours

Sources & evidence

ORD record
ord-0c4435f22d7b48cc9384aff56273c8b8
Source dataset
uspto-grants-1991_09
Patent number
US05047432

Reaction notes

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