Acetic Acid → N-Methyl-N-phenyl-glycine

HRID 724833Notes

Reaction equation

HRID 724833 reaction equation
[C:1]1([NH:7][CH2:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.[BH3-][C:15]#N.[Na+].CC(O)=O>C(#N)C>[CH3:15][N:7]([CH2:8][C:9]([OH:11])=[O:10])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 66025N-PhenylglycineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 420843N-Methyl-N-phenyl-glycineYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-phenylglycine (5 g, 33 mmol) and formaldehyde (37% aqueous solution, 20 mL) in acetonitrile (100 mL) was added NaBH3CN (6.8 g) and AcOH (2 mL) and the reaction mixture was stirred at room temperature overnight. Volatiles were removed in vacuo, the residue was acidified to pH=3-4 and extracted with CHCl3 several times. The combined organic extracts were dried and concentrated to afford a crude product (5.73 g), which was purified by chromatography on silica gel (EtOAc) to afford the title compound (3.96 g, 73%).

Workup

  1. customVolatiles were removed in vacuo
  2. extractionextracted with CHCl3 several times
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated
  5. customto afford a crude product (5.73 g), which
  6. customwas purified by chromatography on silica gel (EtOAc)

Sources & evidence

ORD record
ord-bf036da53cfd4e94b30a013dbb28b1dd
Source dataset
uspto-grants-1998_01
Patent number
US05705504

Reaction notes

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