Hydrochloric Acid → HCID 178484085, compound

Participants

Reaction Conditions

Reaction Steps

0.60 g (2.89 mmol) of trans-4-methylaminomethyl-cyclohexanecarboxylic acid·HCl were mixed with 7.57 mL (36.28 mmol, 12.5 eq) of hexamethyldisilazane and heated under reflux to 140° C. for 2.5 h. The solution was evaporated, dissolved in 6 mL of THF and treated with 0.45 mL (3.18 mmol, 1.1 eq) of 4-chlorophenylchloroformate at 0° C. and stirred at RT overnight. Then 3 mL of water were added at RT followed by 10 mL of 1M NaOH. After stirring for 1 h at RT 15 mL of 1M HCl were added. The solution was then partitioned between EtOAc (×3)/H2O, dried over Na2SO4 and evaporated to yield 0.92 g (98%) of trans-4-{[(4-chloro-phenoxycarbonyl)-methyl-amino]-methyl}-cyclohexane carboxylic acid, MS: 324 (M−H−, 1Cl).

Provenance & Evidence