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

HRID 1940366Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([C:8](=[C:13]2[CH:20]3[CH2:21][CH:16]4[CH2:17][CH:18]([CH2:22][CH:14]2[CH2:15]4)[CH2:19]3)[O:9][CH2:10][CH2:11]I)[CH:5]=[CH:6][CH:7]=1.C1COCC1.[NH3:28]>C(=O)=O>[NH2:28][CH2:11][CH2:10][O:9][C:8](=[C:13]1[CH:20]2[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:22][CH:14]1[CH2:15]3)[CH2:19]2)[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=1

Participants

Conditions

Temperature: 40 °C

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) δ1.77-1.96 (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) δ28.16, 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. ##STR32##

Workup

temperatureThe reaction mixture was cooled down
customsolvent evaporated
customto obtain a white solid
extractionThis material was extracted with methylene chloride
washThe combined organic layers were washed with water
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-282e4c3b7e934a0f8892848a819883fc
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05698728

Reaction notes

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