Hydrochloric Acid → 1-Cyclohexyl-4-dimethylamino-2-phenyl-2-buten-1-ol

HRID 1789097Notes

Reaction equation

HRID 1789097 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]([CH3:18])[CH:8]=[CH:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O.[C:19]1(S)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:26]([BH3-])#N.[Na+].[OH-:30].[Na+].Cl>C(Cl)Cl.C(Cl)(Cl)Cl.O.C(OCC)C.CO.C(N(CC)CC)C>[CH:19]1([CH:26]([OH:30])[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:9][CH2:8][N:7]([CH3:18])[CH3:6])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

13

Reactant 6

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 3534603-(Dimethylamino)-1-phenyl-2-propen-1-oneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 538458471-Cyclohexyl-4-dimethylamino-2-phenyl-2-buten-1-ol

Reagents, catalysts & solvents 6

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

Phosphorus oxychloride (2.5 cc) dissolved in methylene chloride (6 cc) is added dropwise at 0° C. to a solution of 3-dimethylaminoacrylophenone (5 g) in methylene chloride (16 cc). After stirring for 15 minutes at 0° C. and then 30 minutes at 20° C., the temperature is again brought down to 0° C. The precipitate formed is dissolved by adding methanol (5 cc). Triethylamine (8 cc) and thiophenol (3.15 cc) dissolved in methylene chloride (10 cc) are added dropwise. After 2 hours 30 minutes' stirring at 20° C., methanol (30 cc) is added followed by sodium cyanoborohydride (1 g) at 0° C. and stirring is continued for 3 hours at 20° C. The mixture is then concentrated under reduced pressure (2.7 kPa) at 40° C. The solid obtained is taken up in chloroform and the solution is filtered. The organic phase is evaporated under reduced pressure (2.7 kPa) at 40° C. The residue obtained is taken up in water and the solution is made alkaline to pH 10 by adding a 35% strength aqueous solution of sodium hydroxide, and then extracted with methylene chloride. The organic phase is dried over sodium sulphate, filtered and then evaporated to dryness under reduced pressure (2.7 kPa) at 40° C. The residue obtained is dissolved in ethyl ether (10 cc). A 3N solution (10 cc) of hydrochloric acid gas in ethyl ether is added to the solution obtained. The precipitate formed is separated off by filtration and then recrystallised from a mixture of ethanol (15 cc) and ethyl ether (20 cc). In this way 1-dimethylamino-3-phenyl-3-phenylthio-2-propene (Z) hydrochloride (3 g) is obtained in the form of white crystals melting at 176° C.

Workup

  1. custom30 minutes
  2. customat 20° C.
  3. customis again brought down to 0° C
  4. customThe precipitate formed
  5. dissolutionis dissolved
  6. additionare added dropwise
  7. stirringAfter 2 hours 30 minutes' stirring at 20° C.
  8. stirringstirring
  9. waitis continued for 3 hours at 20° C
  10. concentrationThe mixture is then concentrated under reduced pressure (2.7 kPa) at 40° C
  11. customThe solid obtained
  12. filtrationthe solution is filtered
  13. customThe organic phase is evaporated under reduced pressure (2.7 kPa) at 40° C
  14. customThe residue obtained
  15. extractionextracted with methylene chloride
  16. dry with materialThe organic phase is dried over sodium sulphate
  17. filtrationfiltered
  18. customevaporated to dryness under reduced pressure (2.7 kPa) at 40° C
  19. customThe residue obtained
  20. customobtained
  21. customThe precipitate formed
  22. customis separated off by filtration
  23. customrecrystallised from a mixture of ethanol (15 cc) and ethyl ether (20 cc)

Sources & evidence

ORD record
ord-2bec0db7777d45418f92d4f32b0400dd
Source dataset
uspto-grants-1987_08
Patent number
US04686309

Reaction notes

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