Sodium hydride → HCID 17875246, compound

HRID 1069114Notes

Reaction equation

HRID 1069114 reaction equation
O[C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH3:8].CN(CCC)C(Cl)=O.[H-].[Na+]>C(#N)C>[C:9]([N:7]([CH2:6][CH2:5][C:4]1[CH:3]=[CH:2][CH:18]=[CH:17][CH:16]=1)[CH3:8])([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11075917tert-butyl N-[2-(3-hydroxyphenyl)ethyl]-N-methylcarbamateHCID 15040338N-methyl-N-propylcarbamoyl chloride

Product 1

HCID 17875246HCID 17875246, compoundYield 128.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To an ice-cooled solution of 3-hydroxy-N-Boc,N-methyl phenethylamine (5.0 g, 19.9 mmol) in dry acetonitrile (65 ml) was added under nitrogen, N-methyl,N-n-propyl carbamoyl chloride (4.66 g, 34.43 mmol), followed by the portionwise addition of NaH (60% disp. in oil, 1.03 g, 25.87 mmol). The reaction mixture was stirred at RT under nitrogen for 6 hrs and evaporated to dryness in-vacuo. Water (200 ml) was added, the pH was adjusted to ˜9 and the aqueous layer was extracted with ether (4×100 ml). The combined ether layer was washed with NaOH solution (pH 9.5), water (150 ml), dried (Na2SO4) and evaporated to dryness in-vacuo to give an oil which was purified by column chromatography (hexane:EtOAc 2:1), affording 6.0 g (86%) of the title compound as a yellow oil.

Workup

  1. additionwas added under nitrogen
  2. customevaporated to dryness in-vacuo
  3. additionWater (200 ml) was added
  4. extractionthe aqueous layer was extracted with ether (4×100 ml)
  5. washThe combined ether layer was washed with NaOH solution (pH 9.5), water (150 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated to dryness in-vacuo
  8. customto give an oil which
  9. customwas purified by column chromatography (hexane:EtOAc 2:1)

Sources & evidence

ORD record
ord-7c82c20291c142aba420a3b403518719
Source dataset
uspto-grants-2001_06
Patent number
US06251938B1

Reaction notes

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