Hydrochloric Acid → 3-Aminoadamantane-1-carboxylic acid hydrochloride

HRID 1942227Notes

Reaction equation

C([NH:4][C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][C:7]([C:15]([OH:17])=[O:16])([CH2:8]3)[CH2:6]1)[CH2:12]2)(=O)C.[ClH:18]>O>[ClH:18].[NH2:4][C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][C:7]([C:15]([OH:17])=[O:16])([CH2:8]3)[CH2:6]1)[CH2:12]2

Participants

Conditions

Temperature: 95 °C

Procedure

To a 3-neck 5 L, flask equipped with a reflux condenser, a mechanical stirrer and a temperature probe was added 3-acetylamino-adamantane-1-carboxylic acid (432 g, 1.82 mol), water (1.00 L) and concentrated hydrochloric acid (2.44 L), and the resulting mixture was heated at 95° C. for 6 days. During this time, solid material precipitated from the solution. After cooling at 0° C., the solids were filtered and washed with acetone. The solid was then dried under high vacuum at 50° C. for about 2 hours to afford 328 g (78%) of the title compound, 3-amino-adamantane-1-carboxylic acid hydrochloride, as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 12.35 (br s, 1H), 8.27 (br s, 3H), 2.22-2.12 (m, 2H), 1.92-1.85 (m, 2H), 1.83-1.71 (m, 6H), 1.69-1.48 (m, 4H).

Workup

customTo a 3-neck 5 L, flask equipped with a reflux condenser, a mechanical stirrer
customDuring this time, solid material precipitated from the solution
temperatureAfter cooling at 0° C.
filtrationthe solids were filtered
washwashed with acetone
customThe solid was then dried under high vacuum at 50° C. for about 2 hours

Sources & evidence

ORD record: ord-1f3a5389c2c74a3d8ca6acc8a87855fd
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389519B2

Reaction notes

Loading…