cyclopropane-1,1-diyldiMethanaMine dihydrochloride synthesis

Yield:136476-40-9 67%

Reaction Conditions:

Stage #1: 1,1-bis(azidomethyl)cyclopropanewith triphenylphosphine in tetrahydrofuran;water at 40; for 2.5 h;
Stage #2: with hydrogenchloride in dichloromethane;water;

Steps:

16b Cyclopropane-1,1-diyldimethanamine dihydrochloride

5.9 g of 1,1-bis(azidomethyl)cyclopropane is diluted in 123 mL of THF, 41.4 g of PPh3 solubilized beforehand in 62 mL of THF are added dropwise. After 30 mins of stirring at RT, 2.8 mL of water are added and the mixture is heated to 40° C. for 2 h. The reaction medium is dry evaporated and then the residue is taken up in 125 mL of CH₂Cl₂. The 1,1-bis(azidomethyl)cyclopropane is extracted as a salt with a 10% HCl solution. The obtained precipitate is filtered and then dried in the oven. 4.5 g (yield=67%) of cyclopropane-1,1-diyldimethanamine dihydrochloride are obtained as a white powder used as such.

References:

US2013/289031,2013,A1 Location in patent:Paragraph 0613-0614