Morpholine → HCID 53373580, compound

HRID 400395Notes

Reaction equation

HRID 400395 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][CH:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[C:21]([C:23]#[N:24])[CH:20]=[CH:19][C:18]=2[O:25][C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:6].C(=O)([O-])[O-].[K+].[K+].[NH:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1>C(#N)C.CC(C)=O>[C:23]([C:21]1[CH:20]=[CH:19][C:18]([O:25][C:26]2[CH:27]=[C:28]([Cl:33])[CH:29]=[C:30]([Cl:32])[CH:31]=2)=[C:17]([S:14]([N:11]2[CH2:10][CH2:9][CH:8]([NH:7][C:5]([NH:4][CH2:3][CH2:2][N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)=[O:6])[CH2:13][CH2:12]2)(=[O:15])=[O:16])[CH:22]=1)#[N:24]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 53390500HCID 53390500, compound

Product 1

HCID 53373580HCID 53373580, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6342AcetonitrileSolvent

Procedure

1-(2-chloroethyl)-3-(1-(5-cyano-2-(3,5-dichlorophenoxy)-phenylsulfonyl)piperidin-4-yl)urea (838 mg), potassium carbonate (655 mg, 3.0 eq.) and morpholine (413 mg, 3.0 eq.) were dissolved in acetonitrile (25 mL) and heated to reflux. After three hours, the reaction was complete (confirmed by HPLC). The mixture was then concentrated in vacuo, the solid triturated with dichlormethane and isopropyl ether to obtain a white powder. The powder was suspended in hot acetone, cooled in an ice bath, filtered, and washed with water to obtain the product as a white powder (601 mg, 65% yield, 97% purity).

Workup

  1. temperatureheated to reflux
  2. concentrationThe mixture was then concentrated in vacuo
  3. customthe solid triturated with dichlormethane and isopropyl ether
  4. customto obtain a white powder
  5. temperaturecooled in an ice bath
  6. filtrationfiltered
  7. washwashed with water

Sources & evidence

ORD record
ord-0eb4796045284882bf8753bca5101544
Source dataset
uspto-grants-2014_06
Patent number
US08741894B2

Reaction notes

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