Reaction #81040

Reaction equation

[(3-hydroxyphenyl)(2-iodoethoxy)methylene]adamantane

THF

ammonia

→

product

Yield 90.0%

[(2-Aminoethoxy)(3-hydroxyphenyl)methylene]adamantane

Yield 90.0%

Solvents

dry ice

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was cooled down
2. 2
   Othersolvent evaporated
3. 3
   Otherto obtain a white solid
4. 4
   ExtractionThis material was extracted with methylene chloride
5. 5
   WashThe combined organic layers were washed with water
6. 6
   Dryingdried over MgSO4
7. 7
   Concentrationconcentrated

Procedure

A solution of [(3-hydroxyphenyl)(2-iodoethoxy)methylene]adamantane (3.0 g, 0.01 mol) in a minimum amount of THF was added into 10 mL of liquid ammonia in a sealed tube which was kept in dry ice. After sealing the tube this was heated at 40° C. in an oil bath for 17 h. The reaction mixture was cooled down and solvent evaporated to obtain a white solid. This material was extracted with methylene chloride. The combined organic layers were washed with water, dried over MgSO4, and concentrated to give 2.0 g (90%) of the product as a white solid: mp 55° C.; 1H NMR (CDCl3) δ 1.77-1.96 (m, 12H), 2.68 (bs, 1H), 2.85 (t, 2H, J=4.8 MHz), 3.23 (bs, 1H), 3.48 (t, 2H, J=4.8 MHz), 4.46 (bs, 2H), 6.70-7.17 (m, 4H); 13C NMR (CDCl3) δ 28.16, 30.28, 32.19, 36.99, 38.88, 39.04, 41.33, 70.45, 114.97, 116.17, 120.63, 129.02, 131.89, 136.69, 141.79, 156.86; MS m/e (rel intensity) 299 (10), 256 (100), 239 (5), 199 (6), 135 (12), 121 (27), 93 (12), 77 (5). Exact mass: calcd 299:1885, found: 299.1891. ##STR33##

Source