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Short Note

(R,S)-N-[(2-Oxocyclohexyl)methyl]-1-butanaminium Chloride

by
Edmont V. Stoyanov
* and
Ivo C. Ivanov
Faculty of Pharmacy, Medical University of Sofia, Dunav 2, BG-1000 Sofia, Bulgaria
*
Author to whom correspondence should be addressed.
Molecules 2001, 6(6), M215; https://doi.org/10.3390/M215
Submission received: 20 January 2000 / Accepted: 15 May 2001 / Published: 25 May 2001
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 06 m215 i001
The Mannich bases of cyclohexanone with benzylamine and 3,4-methylenedioxybenzylamine hydrochlorides have been prepared in moderate yields using aqueous formaldehyde solution [1]. We report now the synthesis of an analogous product from n-butylamine. A mixture of cyclohexanone (2.00 g, 0.02 mol), paraformaldehyde (1.20 g, 0.04 mol) and n-butylamine hydrochloride (2.22 g, 0.02 mol) was refluxed under stirring in anhydrous ethanol (15 mL) for 5 h (TLC monitoring). The reaction mixture gradually turned into a solution. The solvent was then removed under reduced pressure and the residue was triturated with ice-cooled acetone (20 mL). The separated crystals were filtered, washed with cold acetone, recrystallized from n-butanol and air-dried. Yield: 2.85 g (61 %) of the title compound as colorless crystals.
TLC homogeneous product (TLC: silica gel Merck GF254 Al-sheets, eluted by chloroform-ethanol 3:1).
Mp. 139-140 °C (n-butanol).
1H NMR (300 MHz, d6-DMSO): 0.87 (t, J = 7.4 Hz, CH3), 1.22-1.41 (m, 3H), 1.47-1.70 (m, 4H), 1.70-1.83 (m, 1H), 1.95-2.05 (m, 1H), 2.17-2.32 (m, 2H), 2.36-2.49 (m, 1H), 2.67-2.78 (m, 1H), 2.83 (dd, J1≫J2≫ 6 Hz, 2H, COCHCH2N), 2.97 [sextet, J = 6.2 Hz, 1H, COCH(CH2)2], 3.10-3.20 (m, 1H), 9.0 (br. s, N+H2).
FT IR (fluorolube): 3050-3400, 2942, 2937, 2747, 2566, 2458, 1713 (C=O), 1622, 1588, 1478, 1460, 1445, 1390, 1345.
EI MS [70 eV; m/z (%)]: 184 (2; MH+), 183 (9; M.+), 140 (53), 86 (100), 44 (64), 30 (45); FAB MS [glycerol; m/z (%)]:403 (17; M+2 glycerol+HCl), 367 (1; 2M+H+), 276 (4; 2M+H+), 184 (100; MH+ = C11H22NO+), 140 (2), 86 (27), 44 (3).
Anal. calcd. for C11H22NOCl (219.76): C 60.12, H 10.09, N 6.37, Cl 16.13; found C 60.04, H 9.99, N 6.33, Cl 16.43.

Supplementary materials

Supplementary File 1Supplementary File 2

References

  1. Mannich, C.; Hieronimus, O. Ber. Dtsch. Chem. Ges. 1942, 75, 49–55.
  • Sample Availability: Available from the authors and from MDPI.

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MDPI and ACS Style

Stoyanov, E.V.; Ivanov, I.C. (R,S)-N-[(2-Oxocyclohexyl)methyl]-1-butanaminium Chloride. Molecules 2001, 6, M215. https://doi.org/10.3390/M215

AMA Style

Stoyanov EV, Ivanov IC. (R,S)-N-[(2-Oxocyclohexyl)methyl]-1-butanaminium Chloride. Molecules. 2001; 6(6):M215. https://doi.org/10.3390/M215

Chicago/Turabian Style

Stoyanov, Edmont V., and Ivo C. Ivanov. 2001. "(R,S)-N-[(2-Oxocyclohexyl)methyl]-1-butanaminium Chloride" Molecules 6, no. 6: M215. https://doi.org/10.3390/M215

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