Dimethylamine → HCID 178490547, compound

HRID 2225543Notes

Reaction equation

HRID 2225543 reaction equation
[CH3:1][NH:2][CH3:3].[CH3:4][C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12](=[O:27])[CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23]Cl)=[C:17]([O:25][CH3:26])[CH:16]=2)[CH2:7][CH2:6]1.[Cl-].[Na+].C(Cl)Cl>CC(CC(C)C)=O>[CH3:4][C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12](=[O:27])[CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][N:2]([CH3:3])[CH3:1])=[C:17]([O:25][CH3:26])[CH:16]=2)[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 5234Sodium ChlorideHCID 6344DichloromethaneHCID 178490529HCID 178490529, compound

Product 1

HCID 178490547HCID 178490547, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
110 °C

Procedure

40 ml of a 50% aqueous dimethylamine solution was added to a solution of 2 g of N-(cis-4-methylcyclohexyl)-4-(2-chloroethoxy)-3-methoxycinnamamide (Example 106) in 40 ml of methylisobutylketone. The solution was reacted for 18 hours by heating heated to 110° C., in a closed system. After reaction, the reaction solution was added with 200 ml of an aqueous sodium chloride solution and 100 ml of methylene chloride, and subjected to extraction. The aqueous layer was extracted twice with 100 ml of methylene chloride. The organic layer obtained was washed twice with an aqueous sodium chloride solution and dried over magnesium sulfate. Thereafter, the solvent was removed in vacuo. The product obtained was recrystallized from methylene chloride/ether, yielding 1.6 g of N-(cis-4-methylcyclohexyl)-4-(2-dimethylaminoethoxy)-3-methoxycinnamamide (a compound of the present invention) as white crystal, which had the following physiochemical properties:

Workup

  1. customThe solution was reacted for 18 hours
  2. temperatureby heating
  3. customAfter reaction
  4. extractionsubjected to extraction
  5. extractionThe aqueous layer was extracted twice with 100 ml of methylene chloride
  6. customThe organic layer obtained
  7. washwas washed twice with an aqueous sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. customThereafter, the solvent was removed in vacuo
  10. customThe product obtained
  11. customwas recrystallized from methylene chloride/ether

Sources & evidence

ORD record
ord-0bab9d4f06334f5b8376b601ec58a1df
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

Loading…