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(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethylamine hydrochloride, Form A

IP.com Disclosure Number: IPCOM000172044D
Publication Date: 2008-Jun-26
Document File: 2 page(s) / 74K

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(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethylamine hydrochloride, Form A

(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethylamine, of the following formula:
NH2

O

is an important intermediate in the preparation of (S)-N-[2-(1,6,7,8-tetrahydro-2H- indeno-[5,4-b]furan-8-yl)ethyl]propionamide, which is the first in a new class of sleep agents that selectively binds to the melatonin receptors in the suprachiasmatic nucleus (SCN), versus binding to GABA receptors, such as with other commercial drugs.
(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethylamine hydrochloride can be crystallized using several different procedures. For example, by dissolving the salt in methanol under reflux, and adding an anti-solvent such as acetone to induce the precipitation.

The processes described above may result in a crystalline form of the salt, designated as Form A. Main characteristic peaks in the XRD diffractogram of the mentioned Form A are: 12.2, 12.4, 16.3, 18.2, 23.4, 23.8, 24.4, 25.6, 27.9 and 30.6 ± 0.2 degrees two theta.

The XRD diffractogram of (S)-2-(1,6,7,8-Tetrahydro-2H-indeno[5,4-b]furan-8- yl)ethylamine hydrochloride Form A is described in Figure 1:

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Figure 1. Powder X-ray diffractogram of Form A of (S)-2-(1,6,7,8-tetrahydro-2H- indeno[5,4-b]furan-8-yl]ethylamine hydrochloride.

Example 1:
(S)-2-(1,6,7,8-Tetrah...