Reaction #53852

Reaction equation

2-ethylaminoethanol

trans-[4-(2-Chloro-ethylsulfanylmethyl)-cyclohexyl]-methyl-carbamic acid 4-chloro-phenyl ester

NaI

2-ethylaminoethanol

→

trans-(4-{2-[Ethyl-(2-hydroxy-ethyl)-amino]-ethylsulfanylmethyl}-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester

Solvents

DMA

Conditions

Workup

1. 1
   workup.STIRRINGThe reaction mixture was stirred for 1 week
2. 2
   ConcentrationThe solution was concentrated
3. 3
   Extractionthe residual oil was extracted with aqueous sat. NaHCO3/Et2O (3×)
4. 4
   WashThe organic phases were washed with aqueous 10% NaCl solution
5. 5
   Dryingdried over Na2SO4

Procedure

A solution of 94 mg (0.25 mmol) of trans-[4-(2-Chloro-ethylsulfanylmethyl)-cyclohexyl]-methyl-carbamic acid 4-chloro-phenyl ester in 1 ml DMA was treated with a catalytic amount of NaI and with 0.05 ml (0.5 mmol) of 2-ethylaminoethanol and stirred at RT for 16 h. The reaction mixture was stirred for 1 week, adding every day twice 0.05 ml (0.5 mmol) of 2-ethylaminoethanol. The solution was concentrated and the residual oil was extracted with aqueous sat. NaHCO3/Et2O (3×). The organic phases were washed with aqueous 10% NaCl solution and dried over Na2SO4 to yield after flash column chromatography on silica gel (CH2Cl2/MeOH 95:5) 40 mg (39%) of trans-(4-{2-[Ethyl-(2-hydroxy-ethyl)-amino]-ethylsulfanylmethyl}-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester, MS: 429 (MH+, 1Cl).

Source