- Nitrolysis of Tertiary Amines: Piperidines, Piperazines, Bisdimethylaminoalkanes, and Functionalized Methyldialkylamines
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Preparative amounts of mono- and di-nitrosamines were obtained from aliphatic cyclic and acyclic tertiary monamines and diamines by treatment with dinitrogen tetraoxide in carbon tetrachloride at 0 - 45 deg C.N-Methyl- and N-ethyl-piperidines (1) and (2) gave N-nitrosopiperidine (15), but N-isopropyl- and N-t-butyl-piperidines (3) and (4) did not.N-Methyl-, N-ethyl-, N-isopropyl- and N-t-butyl-N'-methylpiperazines (5) - (8) gave N,N'-dinitrosopiperazine (22) (in 90 percent, 81 percent, 55 percent, and 8 percent yields, respectively) and the diamine (8) also gave N-t-butyl-N'-dinitrosopiperazine (23) (45 percent).The N'-nitroso and the N'-nitro derivatives of N-methylpiperazine were similarly converted into N,N'-dinitroso- and N-nitroso-N'-nitropiperazines (22) (45 percent) and (30) (53 percent).Bisdimethylaminoalkanes (Me2N)2(CH2)n (10) - (14) gave bismethylnitrosaminoalkanes 2(CH2)n (24) - (27) and dimethylnitrosamine (28): n=1 (0 percent, 90 percent); n=2 (68 percent, 0 percent); n=3 (48 percent, 43 percent); n=4 (41 percent, 38 percent); n=6 (58 percent, 35 percent). β-Dimethylaminopropionitrile (18), 1-methylnitrosamino-2-dimethylaminoethane (17), and α-dimethylaminoacetic acid (19) gave the corresponding nitrosoamines by replacement of an N-methyl group.
- Boyer, Joseph H.,Kumar, Govindarajulu,Pillai, T. Perumal
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p. 1751 - 1754
(2007/10/02)
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