Reaction #2446107

Reaction equation

Compound 1

3-(4-chlorophenyl)adamantane-1-carboxylic acid [2-(3,4-dihydroxyphenyl)ethyl]amide

→

Compound 2

Yield 54.0%

acetic acid 2-acetoxy-4-(2-{[3-(4-chlorophenyl)adamantane-1-carbonyl]amino}ethyl)phenyl ester

Yield 54.0%

Solvents

acetic anhydride

H2SO4

Conditions

Workup

1. 1
   ConcentrationThe solution was then concentrated under a vacuum
2. 2
   Filtrationfiltered

Procedure

Compound 1 (1 g) was dissolved in 10 mL of acetic anhydride with a catalytic amount of 98% H2SO4 and stirred under N2 for 3 days at room temperature. The solution was then concentrated under a vacuum and filtered to give the product Compound 2 (yield=54%), with a melting point of 160-162° C. 1H NMR (500 MHz, CDCl3) δ 1.74 (m, 2H, Admant-H), 1.81-1.88 (m, 8H, Admant-H), 1.93 (s, 2H, Admant-H), 2.26-2.27 (m, 2H, Admant-H), 2.28 (s, 3H, COCH3), 2.31 (s, 3H, COCH3), 2.83-2.85 (t, J=5 Hz, 2H, CH2), 3.50-3.54 (q, 2H, NCH2), 5.69 (s, 1H, NH), 7.01-7.02 (d, J=5 Hz, 1H, Ar—H), 7.07-7.09 (d, d, 1H, H—Ar), 7.13-7.15 (d, J=10 Hz, 1H, Ar—H), 7.30 (s, 4H, Ar—H). 13C NMR (500 MHz, CDCl3) δ 20.6, 20.7, 28.8, 35.0, 35.5, 36.5, 38.3, 40.2, 40.3, 41.7, 42.0, 44.5, 123.5, 124.0, 126.4, 127.0, 128.3, 131.5, 138.0, 140.6, 142.0, 148.4, 168.4, 168.5, 177.5. Mass spectroscopy m/z (relative intensity) 510.24 (M+, 100), 511.24 (38), 512.24 (45).

Source