4-Methylmorpholine → 2-Mesylamino-4-[4-(diphenylmethoxy)piperidinomethyl]thiazole

HRID 1649846Notes

Reaction equation

HRID 1649846 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([O:14][CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)[N:6]=1.CN1CCOCC1.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>CN(C)C=O.ClCCl>[S:36]([NH:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([O:14][CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:10][CH2:9]2)[N:6]=1)([CH3:35])(=[O:38])=[O:37]

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 31297Methanesulfonyl chlorideHCID 198549372-Amino-4-[4-(diphenylmethoxy)piperidinomethyl]thiazole

Product 1

HCID 198549402-Mesylamino-4-[4-(diphenylmethoxy)piperidinomethyl]thiazoleYield 34%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 2-amino-4-[4-(diphenylmethoxy)piperidinomethyl]thiazole (0.78 g), N-methylmorpholine (1.15 ml) in N,N-dimethylformamide (8 ml) was added dropwise a solution of methanesulfonyl chloride (0.5 g) in dichloromethane (0.5 ml) under ice-bath cooling. After 1 hour, the reaction mixture was filtered. The filtrate was made basic with 1N sodium hydroxide solution (12 ml). After being stirred for 30 minutes, the mixture was neutralized with 1N hydrochloric acid and extracted with dichloromethane (40 ml×2). The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was distilled off and the residue was subjected to column chromatography on silica gel, and eluted with a mixture of chloroform and methanol (10:1 V/V). The fractions containing the object compound were combined and concentrated under reduced pressure to give white crystals. The crystals were recrystallized from ethanol to give 2-mesylamino-4-[4-(diphenylmethoxy)piperidinomethyl]thiazole (0.32 g).

Workup

  1. temperaturecooling
  2. filtrationthe reaction mixture was filtered
  3. extractionextracted with dichloromethane (40 ml×2)
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off
  7. washeluted with a mixture of chloroform and methanol (10:1 V/V)
  8. additionThe fractions containing the object compound
  9. concentrationconcentrated under reduced pressure
  10. customto give white crystals
  11. customThe crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-20abea351a314b408930ea4d8e02c440
Source dataset
uspto-grants-1990_05
Patent number
US04921887

Reaction notes

Loading…