1,3-Bis(pyrrolidin-2-on-1-yl)but-1-ene
Jin-Cong Zhuo
College of Pharmacy, The Ohio State University, 500 West 12th Avenue, Columbus, OH 43210, USA. Fax: (614) 292 2435; E-mail: [email protected]
Received: 17 September 1999 / Accepted: 4 October1999 / Published: 23 November 1999
To a solution of 1-vinyl-2-pyrrolidinone (1, 11.1 g, 100 mmol) in CH2Cl2 (100 ml) was added a drop of CF3CO2H at room temperature. The resulting solution was stood at room temperature for 24 h. The solvent was evaporated under reduced pressure. The residue is the desired product 2 (11.1 g, 100%). The product can be recrystallise from acetone.
M.p. 73.2-74.8ºC (Lit. [1]: 75ºC).
IR(cm-1, neat): 3070m, 1700vs, 1690vs, 1675vs, 1655vs, 1405vs, 1285vs, 1240s, 955s, 730s.
1H-NMR(CDCl3): 7.00 (d, J = 14.2, 1H, H-1), 4.94 (dd, J = 14.2, 6.0, 1H, H-2), 4.89 (m, 1H, H-3), 3.49 (t, J = 7.2, 2H, NCH2), 3.30 (m, 2H, NCH2), 2.50 (t, J = 8.1, 2H, COCH2), 2.40 (t, J = 8.1, 2H, COCH2), 2.12 (m, 2H, CH2), 2.00 (m, 2H, CH2), 1.30 (d, J = 7.0, 3H, Me).
13C-NMR(CDCl3): 174.2 (C, NCO), 173.3 (C, NCO), 125.1 (CH, C-1), 110.7 (CH, C-2), 46.0 (CH, C-3), 45.2 (CH2, NCH2), 42.4 (CH2, NCH2), 31.4 (CH2, COCH2), 31.2 (CH2, COCH2), 18.0 (CH2), 17.4 (CH3, C-4), 17.0 (CH2).
EI-MS: 223 (M+H+, 6), 222 (M+, 36), 207 (M+-Me, 37), 204 (27), 179 (13), 138 (36), 124 (34), 122 (21), 112 (43), 110 (29), 109 (32), 98 (26), 96 (20), 94 (24), 82 (41), 81 (100), 80 (24), 70 (27), 69 (55), 56 (23), 55 (35).
References
| 1. | Breitenbach, J. W.; Galinovsky, F.; Nervadbar, H.; Wolf, E. Monatsh. Chem. 1956, 87, 580. |
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