2-Morpholinoethylamine → HCID 68511474, compound

HRID 1929333Notes

Reaction equation

HRID 1929333 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:13]=[C:12]([NH:14][C:15](=[O:18])OC)[NH:11][C:10]=2[CH:19]=1.[N:25]1([CH2:31][CH2:32][NH2:33])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>CN1CCCC1=O.C(OCC)C>[Cl:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:13]=[C:12]([NH:14][C:15]([NH:33][CH2:32][CH2:31][N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:18])[NH:11][C:10]=2[CH:19]=1

Participants

5

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 86646931HCID 86646931, compound

Product 1

HCID 68511474HCID 68511474, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

put a solution of 250 mg of methyl {6-[(2,6-dichlorobenzyl)oxy]-1H-benzimidazol-2-yl}carbamate and 178 mg of 2-morpholin-4-ylethanamine in 3 cm3 of 1-methylpyrrolidin-2-one in a microwave reactor. After the reactor has been sealed, it is put in the microwave cavity for 25 minutes at 125° C. The reaction mixture is then evaporated to dryness under reduced pressure (0.2 kPa) with a bath temperature of 85° C. The residue is taken up in 30 cm3 of water, then extracted three times with 180 cm3 of ethyl acetate. The combined organic phases are washed three times with 30 cm3 of water, dried over magnesium sulphate, filtered and evaporated under reduced pressure (2 kPa). After purification of the residue by silica-column flash chromatography [eluent: dichloromethane/methanol (90/10 by volume)], the product obtained is solidified in 20 cm3 of diethyl oxide, filtered, washed three times with 3 cm3 of diethyl oxide and dried under reduced pressure in the presence of potassium hydroxide. We obtain 241 mg of 1-{6-[(2,6-dichlorobenzyl)oxy]-1H-benzimidazol-2-yl}-3-(2-morpholin-4-ylethyl)urea in the form of a pink powder, which has the following characteristics:

Workup

  1. customAfter the reactor has been sealed
  2. customThe reaction mixture is then evaporated to dryness under reduced pressure (0.2 kPa) with a bath temperature of 85° C
  3. extractionextracted three times with 180 cm3 of ethyl acetate
  4. washThe combined organic phases are washed three times with 30 cm3 of water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure (2 kPa)
  8. customAfter purification of the residue by silica-column flash chromatography [eluent: dichloromethane/methanol (90/10 by volume)]
  9. customthe product obtained
  10. filtrationfiltered
  11. washwashed three times with 3 cm3 of diethyl oxide
  12. dry with materialdried under reduced pressure in the presence of potassium hydroxide

Sources & evidence

ORD record
ord-8ad161dd79b740c09a17b81b3f943b00
Source dataset
uspto-grants-2012_05
Patent number
US08188078B2

Reaction notes

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