Methanol → Cyclopropanecarboxylic acid, 1-(methylamino)-, methyl ester, hydrochloride (9CI)

HRID 2248954Notes

Reaction equation

HRID 2248954 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][NH:6][C:7]1([C:10]([OH:12])=[O:11])[CH2:9][CH2:8]1.[CH3:13]O>>[ClH:3].[CH3:5][NH:6][C:7]1([C:10]([O:12][CH3:13])=[O:11])[CH2:9][CH2:8]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 3861971-methylamino-cyclopropane-1-carboxylic acid

Product 1

HCID 19995335Cyclopropanecarboxylic acid, 1-(methylamino)-, methyl ester, hydrochloride (9CI)Yield 86.6%

Procedure

86.5 g (1.2 mol) of thionyl chloride were added dropwise to 300 ml of methanol at -10° C., and thereafter 36.9 g (0.32 mol) of 1-methylamino-cyclopropane-1-carboxylic acid were introduced in portions. Stirring was carried out for 5 hours at room temperature, and the mixture was allowed to stand overnight. The mixture was worked up by filtering it, evaporating down the filtrate in vacuo and heating the residue together with 7 g of active carbon for 10 minutes in methanol. After filtration and evaporation, 45.9 g (86.6% of theory) of methyl 1-methylamino-cyclopropane-1-carboxylate hydrochloride were obtained as a yellowish viscous oil of refractive index nD23.5 : 1.4798.

Workup

  1. waitto stand overnight
  2. filtrationby filtering it
  3. customevaporating down the filtrate in vacuo
  4. temperatureheating the residue together with 7 g of active carbon for 10 minutes in methanol
  5. filtrationAfter filtration and evaporation

Sources & evidence

ORD record
ord-4c92e9f41b4d4213b43a084e94c35d08
Source dataset
uspto-grants-1991_08
Patent number
US05041612

Reaction notes

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