Hydrochloric Acid → HCID 57425668, compound

HRID 1360113Notes

Reaction equation

HRID 1360113 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].C[Al](C)C.[N:10]1([CH:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17]([O:19]C)=O)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.Cl>>[CH3:5][O:4][N:3]([CH3:2])[C:17](=[O:19])[CH:16]([N:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 16682925TrimethylaluminumHCID 57425659HCID 57425659, compound

Product 1

HCID 57425668HCID 57425668, compound

Conditions

Temperature
0 °C

Procedure

N,O-Dimethylhydroxylamine hydrochloride (1.66 g, 17.0 mmol) was suspended in 20 mL of dry TVF and cooled to 0° C. Trimethylaluminum (8.50 mL, 2.0M solution in toluene, 17.0 mmol) was added slowly and stirred for 30 minutes. Methyl morpholin-4-yl-(phenyl)acetate (1.00 g, 4.25 mmol) was added to the cooled mixture in an 8 mL TIFF solution. The reaction was allowed to warm to ambient temperature while for 18 hours. The mixture was poured into 1N HCl(aq) and stirred for 1 hour. The mixture was then poured into NaHCO3(sat) and extracted 3× with EtOAc. The combined organic layers were washed 1× with brine, dried with Na2SO4, filtered and concentrated in vacuo to provide N-methoxy-N-methyl-2-morpholin-4-yl-2-phenylacetamide. HRMS [M+H] C14H21N2O3 calc'd 265.1547. found 265.1553.

Workup

  1. temperatureto warm to ambient temperature while for 18 hours
  2. stirringstirred for 1 hour
  3. extractionextracted 3× with EtOAc
  4. washThe combined organic layers were washed 1× with brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0059a27073534047b34f6635a7c1010a
Source dataset
uspto-grants-2011_02
Patent number
US07879839B2

Reaction notes

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