Morpholine → HCID 54008544, compound

HRID 634600Notes

Reaction equation

HRID 634600 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:7][C:8]([N:10](C)C)=O.[CH2:13]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33](Cl)=[S:34])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>C1(C)C=CC=CC=1>[O:4]1[CH2:5][CH2:6][N:1]([CH2:7][CH2:8][NH:10][C:33](=[S:34])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 31374DimethylacetamideHCID 54146617HCID 54146617, compound

Product 1

HCID 54008544HCID 54008544, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a 200 ml flask equipped with a stirrer, a condenser and a calcium chloride dryer tube were charged 2.6 g of morpholine and 50 ml of DMAc and the mixture was stirred under ice-cooling. To the solution was gradually added dropwise 7.5 g of 11-decylthioundecanoic acid chloride prepared in Synthetic example 13. After completion of dropwise addition, the mixture was returned to room temperature and further stirred for 2 hours. The reaction solution was diluted with 300 ml of toluene, and washed successively with a 5% aqueous sodium hydrogen carbonate solution, distilled water and a saturated saline solution. The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to obtain crystals. The crystals were recrystallized from n-hexane to obtain 6.9 g of the title compound. Melting point: 61° C.

Workup

  1. customIn a 200 ml flask equipped with a stirrer, a condenser and a calcium chloride dryer tube
  2. temperaturecooling
  3. customprepared in Synthetic example 13
  4. additionAfter completion of dropwise addition
  5. customwas returned to room temperature
  6. stirringfurther stirred for 2 hours
  7. washwashed successively with a 5% aqueous sodium hydrogen carbonate solution
  8. distillationdistilled water
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. customthe solvent was removed under reduced pressure
  11. customto obtain crystals
  12. customThe crystals were recrystallized from n-hexane

Sources & evidence

ORD record
ord-16ee1e43a7ef4150b41b6be2492849dd
Source dataset
uspto-grants-2001_02
Patent number
US06184180B2

Reaction notes

Loading…