N,N'-Dimethylethylenediamine → tert-Butyl methyl(2-(methylamino)ethyl)carbamate

HRID 2392987Notes

Reaction equation

HRID 2392987 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][NH:5][CH3:6].[C:7]([O:11][C:12]([O:14]N=C(C1C=CC=CC=1)C#N)=O)([CH3:10])([CH3:9])[CH3:8].C[O-].[Na+]>CCOCC>[C:7]([O:11][C:12]([N:2]([CH3:1])[CH2:3][CH2:4][NH:5][CH3:6])=[O:14])([CH3:8])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 8070N,N'-DimethylethylenediamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 14403871tert-Butyl methyl(2-(methylamino)ethyl)carbamate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

8.8 g of N,N'-dimethylethylenediamine were dissolved in 50 ml of ether and the solution was cooled to 0° C. 18.5 g of BOC-ON [2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile] were slowly added dropwise and the mixture was stirred at RT for 16 hours. 6 g of sodium methylate were added and stirring was continued at RT for 18 hours. The substance which had precipitated out was filtered off with suction and washed with ether. The combined ether solution was concentrated in vacuo and the residue was distilled (boiling point 58°-60° C./0.5 mbar). 11.3 g were obtained as a colorless oil. MS(Cl): 189 (M+H)⊕, 133

Workup

  1. stirringstirring
  2. waitwas continued at RT for 18 hours
  3. customThe substance which had precipitated out
  4. filtrationwas filtered off with suction
  5. washwashed with ether
  6. concentrationThe combined ether solution was concentrated in vacuo
  7. distillationthe residue was distilled (boiling point 58°-60° C./0.5 mbar)
  8. custom11.3 g were obtained as a colorless oil

Sources & evidence

ORD record
ord-f95f8c488c0247dda354498577aca4a4
Source dataset
uspto-grants-1998_09
Patent number
US05804559

Reaction notes

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