2-butanamine

A solution of 4% aq. H2SO4, (301) was heated to 50"C over 30-60 min. Nitrogen was bubbled through the solution during this time. 4-(Cyano-methyl)phenylhydrazine hydrochloride (1080g, 4.77 mol) was added as a solid to the heated mixture. After it had dissolved, A,A-dimethyl-4,4-dimethoxy-butanamine (965 g, 5.98 mol) was added over a period of 30 min. The mixture was then heated at reflux for 2 h. The reaction mixture was cooled and diluted with portions of 30%o aq. NH4OH (21 total) over 0.5 h at a rate to maintain the temperature at 25-30°C. The product was then extracted into isopropyl acetate (3 x 101). The solution was concentrated to 31 which led to a precipitate which was isolated by filtration and washed with cold isopropyl acetate to give 827.4 g (76%) of product. 

Chemical Designations - Synonym 1-Butanamine, -butyl Dibutylamine Chemical Formula ... 

A.T. Derivatives of l-(l,3-benxodioxol-5-yl)-2-butanamine Repre sentatives of a novel therapeutic class. J Med Chem 29 2009-2015, 1986. 

Butadiene diepoxide, d546 Butanal, b612 1-Butanamine, b509... 

Butyl bromide, b274 sec-Butyl bromide, b275 tert-Butyl bromide, b372 iV-Butyl-l -butanamine, dl39 Butyl butenoate, b531... 

Synonyms AI3-24197 1-Aminobutane BRN 0605269 Butan-l-amine 1-Butanamine n-Butylamine CCRIS 4756 EINECS-203-699-2 FEMA No. 3130 Monobutylamine Mono-/3-but-ylamine Norralamine Norvalamine NSC 8029 Tutane UN 1125. 

The allylically activated chiral methanimidamides are more reactive and can be prepared from 2,5-dihydro-l//-pyrrole or 1,2,5,6-tetrahydropyridine by heating with a chiral auxiliary substituted methanimidamide in toluene. Deprotonation of the more acidic 1 -iminomethy 1-2,5-dihydro-1//-pyrrole with butyllithium was complete after a few minutes, even at — 100 °C41. Alkylation afforded a mixture of regioisomers, 2-alkylated 2,5-dihydro-l //-pyrrole 1 (n = 1) and 3-alkylated 2,3-dihydro-l//-pyrrole 2 (n = 1), the former strongly predominating (about 92 8). During hydrazinolysis of the 2-substituted 2,5-dihydro-1 //-pyrrole 1 (n = 1) the minor product decomposed, thus separation of the regioisomers was unnecessary. About 80-85% of the chiral auxiliary (S)-l- m-butoxy-3-methyl-2-butanamine was recovered after hydrazinolysis. 

V-Cyclohexylidene-1 -butoxy-2-butanamine was successfully hydrolyzed using 2N hydrochloric acid in tetrahydrofuran at 0 °C for 15 minutes24. 

Amines are named by adding the suffix-amine to the name of (a) the alkyl group attached to N or b) the longest alkane chain. The terminal e in the name of the parent alkane is dropped when amine follows but not when, for example, diamine follows [see Problem 18.1(d)]. Thus, CH3CH(NH2)CHjCHj is named sec-butylamine or 2-butanamine. Amines, especially with other functional groups, are named by considering amino, N-alkylamino and N,N-dialkylamino as substituents on the parent molecule N indicates substitution on nitrogen. 

---