Sodium Bicarbonate → 2-Amino-3,N-dimethyl-N-phenethyl-butyramide

HRID 491915Notes

Reaction equation

HRID 491915 reaction equation
C(OC(=O)[NH:7][CH:8]([C:12](=[O:23])[N:13]([CH3:22])[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:9]([CH3:11])[CH3:10])(C)(C)C.C(=O)(O)[O-].[Na+]>Cl.C(O)(C)C.C(OCC)(=O)C>[NH2:7][CH:8]([CH:9]([CH3:11])[CH3:10])[C:12]([N:13]([CH3:22])[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:23]

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 67023731[2-Methyl-1-(methyl-phenethyl-carbamoyl)-propyl]-carbamic acid tert-butyl ester

Product 1

HCID 548719212-Amino-3,N-dimethyl-N-phenethyl-butyramide

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

[2-Methyl-1-(methyl-phenethyl-carbamoyl)-propyl]-carbamic acid tert-butyl ester (3.79 g, 11.3 mmol) was added slowly in hydrochloric acid in isopropyl alcohol ([5M], 25 mL). The resulting mixture was stirred for 5 hours at room temperature, then the solvent was evaporated under reduced pressure to yield an oil. The oil was dissolved in ethyl acetate and treated with sodium bicarbonate solution. The organic layer was dried with MgSO4, filtered and the solvent evaporated under reduced pressure to yield an oil, which was purified by column chromatgraphy (10-50% EtOAc/heptane) to yield a residue.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customto yield an oil
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure
  6. customto yield an oil, which
  7. customwas purified by column chromatgraphy (10-50% EtOAc/heptane)
  8. customto yield a residue

Sources & evidence

ORD record
ord-e421fd06ca324aab9286c551615775d0
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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