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Molecules 2000, 5, M159

1-(N,N-Dimethylamino)adamantane

Sukanta Bhattacharyya*

Department of Chemistry, The University of Mississippi, University, MS 38677.
*Current Address: Argonaut Technologies, 887 Industrial Road, Suite G, San Carlos, CA 94070, USA. E-mail: [email protected]

Received: 27 February 2000 / Accepted: 22 March 2000 / Published: 28 April 2000

The title compound, an important antiviral agent [1] was prepared from commercially available 1-aminoadamantane by titanium(IV) isopropoxide mediated reductive amination of formaldehyde [2]. A mixture of 1-aminoadamantane (0.38 g, 2.5 mmol), titanium(IV) isopropoxide (1.42 g, 5 mmol) and paraformaldehyde (0.3 g, 10 mmol) was magnetically stirred at 50 ^oC for 2 h. The mixture was then cooled to ambient temperature, after which sodium borohydride (0.190 g, 5 mmol) and absolute ethanol (6 ml) were added. The resulting mixture was further stirred at room temperature for 3 h and at 50 ^oC for 2 h. The reaction was quenched with aqueous ammonia (15 ml, 2 M), the resulting precipitate of TiO₂ was filtered and washed with diethyl ether (2 x 10 ml). The organic layer was separated and the aqueous part was extracted with ether (20 ml x 2). The combined organic extracts were dried (Na₂SO₄) and concentrated to afford 1 as a colorless oil. Flash chromatography of the crude product over neutral alumina using a diethyl ether-hexanes mixture (4:1) furnished analytically pure 1 (0.39 g, 90%) as a colorless liquid.

¹H NMR (300 MHz, CDCl₃):1.55-1.75 (m, 12 H), 2.08 (br s, 3H), 2.26 (s, 6H).

¹³C NMR (75.5 MHz, CDCl₃): 29.6, 37.0, 37.2, 38.1, 53.7, 150.5.

Anal. Calc. for C₁₂H₂₁N: C 80.38, H 11.81, N 7.81. Found: C 80.39, H 12.03, N 7.64.

References

1. Aldrich, P. E.; Hermann, E. C.; Meier, W. E.; Paulshock, M.; Prichard, W. W.; Snyder, J. A.; Watts, J. C. J. Med. Chem., 1971, 14, 535; Wishnok, J. S. J. Chem. Edu., 1973, 50, 780; Shirayev, A.; Kong, P.; Lin, T.; Moiseev, I. G. Synthesis 1997, 38 and references therein; Kirschbaum, J. in Analytical Profiles of Drug Substances, ed. K. Florey, Academic Press, NY, 1983, vol. 12, p. 1.

2. Bhattacharyya, S. Tetrahedron Lett.1994, 35, 2401; Bhattacharyya, S. J. Chem. Soc. Perkin Trans. 1, 1995, 1845.

Sample Availability: Available from the author.

1.	Aldrich, P. E.; Hermann, E. C.; Meier, W. E.; Paulshock, M.; Prichard, W. W.; Snyder, J. A.; Watts, J. C. J. Med. Chem., 1971, 14, 535; Wishnok, J. S. J. Chem. Edu., 1973, 50, 780; Shirayev, A.; Kong, P.; Lin, T.; Moiseev, I. G. Synthesis 1997, 38 and references therein; Kirschbaum, J. in Analytical Profiles of Drug Substances, ed. K. Florey, Academic Press, NY, 1983, vol. 12, p. 1.
2.	Bhattacharyya, S. Tetrahedron Lett.1994, 35, 2401; Bhattacharyya, S. J. Chem. Soc. Perkin Trans. 1, 1995, 1845.