Dimethylformamide → N-(1-Methyl-2-oxo-2-phenylethyl)-4-(phenylmethyl)-2-morpholinecarboxamide

HRID 2367398Notes

Reaction equation

HRID 2367398 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]1([CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH:16]([C:20]([OH:22])=O)[CH2:15]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CN(C=O)C.C(N(CC)CC)C.[NH2:35][CH:36]([CH3:45])[C:37]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:38]>C(Cl)Cl.O>[CH3:45][CH:36]([NH:35][C:20]([CH:16]1[O:17][CH2:18][CH2:19][N:14]([CH2:13][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:15]1)=[O:22])[C:37](=[O:38])[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 107786(-)-alpha-Amino-propiophenoneHCID 27763534-Benzylmorpholine-2-carboxylic acid

Product 1

HCID 58504388N-(1-Methyl-2-oxo-2-phenylethyl)-4-(phenylmethyl)-2-morpholinecarboxamideYield 41.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

Oxalyl chloride (1.17 mL, 13.3 mmol) was added to the suspension of 4-(phenylmethyl)-2-morpholinecarboxylic acid (2.290 g, 8.89 mmol) and DMF (0.034 mL, 0.444 mmol) in CH2Cl2 (60 mL) at 0° C., and the resulting mixture was stirred at 25° C. for 2 hours, and then evaporated. CH2Cl2 (60 mL) was added to the resulting residue, and the resulting brown solution was added to a suspension of triethylamine (4.34 mL, 31.1 mmol) and 2-amino-1-phenyl-1-propanone (1.65 g, 8.89 mmol) in CH2Cl2 (60 mL) at 0° C. The reaction mixture was stirred at 25° C. overnight. Water (150 mL) was added, and the resulting mixture was extracted with EtOAc (3×80 mL). The organics were dried (Na2SO4), filtered, and evaporated. The resulting residue was purified by silica gel chromatography, eluting with EtOAc in PE from 20% to 50% to afford the title compound (1.3 g) as a yellow oil. LC-MS (ES) m/z=353 [M+H]+.

Workup

  1. customevaporated
  2. additionCH2Cl2 (60 mL) was added to the resulting residue
  3. stirringThe reaction mixture was stirred at 25° C. overnight
  4. extractionthe resulting mixture was extracted with EtOAc (3×80 mL)
  5. dry with materialThe organics were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe resulting residue was purified by silica gel chromatography
  9. washeluting with EtOAc in PE from 20% to 50%

Sources & evidence

ORD record
ord-a0244440d1ea49b3a04365dc7ce5db5e
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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