Potassium Carbonate → HCID 19836753, compound

HRID 1608143Notes

Reaction equation

HRID 1608143 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6]Cl)([O-])=O.Cl.[CH2:13]([O:15][C:16](=[O:20])[CH2:17][NH:18][CH3:19])[CH3:14].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:13]([O:15][C:16](=[O:20])[CH2:17][N:18]([CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[NH2:1])[CH3:19])[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 119212-Nitrobenzyl chlorideHCID 171173Ethyl N-methylaminoacetate hydrochloride

Product 1

HCID 19836753HCID 19836753, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 8.6 g o-nitrobenzyl chloride, 7.6 g sarcosine ethyl ester hydrochloride and 13.8 g K2CO3 was refluxed in 300 ml acetone for 16 hours, whereafter the mixture was filtered and evaporated. The oily residue was partitioned between ether/1N HCl. The aqueous phase was separated and pH was adjusted to 10 with dil. NaOH, whereafter it was extracted with dichloromethane. The organic phase was dried over Na2SO4 and evaporated. This left an oil which was hydrogenated using a standard procedure by means of 5% PD/C to give N-(o-aminobenzyl)sarcosine ethyl ester as an oil.

Workup

  1. filtrationwas filtered
  2. customevaporated
  3. customThe oily residue was partitioned between ether/1N HCl
  4. customThe aqueous phase was separated
  5. extractionwas extracted with dichloromethane
  6. dry with materialThe organic phase was dried over Na2SO4
  7. customevaporated
  8. waitThis left an oil which

Sources & evidence

ORD record
ord-192078c13fca4b2c9639e2deed48018d
Source dataset
uspto-grants-1989_09
Patent number
US04870073

Reaction notes

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