Water → HCID 19823628, compound

HRID 728298Notes

Reaction equation

HRID 728298 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([N:16]([CH3:18])[CH3:17])[CH2:13][CH2:14][OH:15])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.O.Cl[CH2:25]Cl>CN(C)C=O>[CH3:18][N:16]([CH:12]([C:8]1([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:9][CH2:10][CH2:11]1)[CH2:13][CH2:14][O:15][CH3:25])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6344Dichloromethane2×HCID 24386Thionyl ChlorideHCID 19823740HCID 19823740, compound

Product 1

HCID 19823628HCID 19823628, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-[1-(4-chlorophenyl)cyclobutyl]-3-dimethylaminopropan-1-ol (7.8 g) in dichloromethane (150 ml) and dimethylformamide (4 ml) was treated at 0° C. with a solution of thionyl chloride (14 ml) in dichloromethane (7 ml). The mixture was stirred at room temperature for 45 minutes, then heated at reflux for 15 hours, cooled, poured into water and washed with dichloromethane. The aqueous phase was basified and extracted with ether. The extract was evaporated and the residue was dissolved in methanol (50 ml) and treated with sodium methoxide (1 g). The solution was heated under reflux for 17 hours and then concentrated to about 10 ml and diluted with water to 150 ml. The aqueous solution was extracted with ether and the extracts back-extracted with 3N hydrochloric acid. The acidic extracts were basified and extracted with ether. The ethereal extracts were dried and evaporated to give an oil which was mixed with petroleum ether (b.p. 40-60) (20 ml). The resulting mixture was filtered and evaporated to give N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methoxypropylamine as an oil the boiling point of which was not determined.

Workup

  1. temperatureheated
  2. temperatureat reflux for 15 hours
  3. temperaturecooled
  4. washwashed with dichloromethane
  5. extractionextracted with ether
  6. customThe extract was evaporated
  7. dissolutionthe residue was dissolved in methanol (50 ml)
  8. additiontreated with sodium methoxide (1 g)
  9. temperatureThe solution was heated
  10. temperatureunder reflux for 17 hours
  11. concentrationconcentrated to about 10 ml
  12. additiondiluted with water to 150 ml
  13. extractionThe aqueous solution was extracted with ether
  14. extractionthe extracts back-extracted with 3N hydrochloric acid
  15. extractionextracted with ether
  16. customThe ethereal extracts were dried
  17. customevaporated
  18. customto give an oil which
  19. filtrationThe resulting mixture was filtered
  20. customevaporated

Sources & evidence

ORD record
ord-a35e8514b9fd4c24b26b584bc6b23b46
Source dataset
uspto-grants-1991_09
Patent number
US05047432

Reaction notes

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