Neopentylamine

Hammerum, S. Derrick, P.J. Thermodynamics of Intermediate Ion-Molecule Complexes or Kinetics of Competing Reactions The Reactions of Low-Energy Isobutylamine and Neopentylamine Molecular Ions. J. Chem. Soc.. Perkin Trans. 2 1986, 1577-1580. 

Neodymium perchlorate. 2acetonitrile, 4142 f Neopentane, see 2,2-Dimethylpropane, 1993 f Neopentylamine, see 2,2-Dimethylpropylamine, 2024 Neptunium hexafluoride, 4360 Nickel azide, All 1 Nickel chlorite, 4087... 

Catalytic hydrogenation of the cyanide function in f-butylcyanide to afford neopentylamine has been achieved with [(C5Me5)2ScH]B, Eq. (19) [52]. 

The isolation of chloro heterocycles is not always necessary. Chlorination with POCI3 and amination can be combined in a one-pot reaction as exemplified by the reaction of 4-phenyl-1-(2//)-phthalazinone (83) with POCI3 in the presence of excess neopentylamine in boiling xylene to furnish 84 in 77% yield (85EUPI5%52). 

Problem 23.12 Predict the organic products of the reaction of (a) isobutylamine with nitrous acid (b) neopentylamine with nitrous add. 

A solution of freshly sublimed t-BuOK (5.60 g, 50 mmol) in anhyd THE (60 mL) was treated with AT-(3-bromo-4,4-dimethy 1-2-pentylidene)neopentylamine (2.62 g, 10 mmol) and stirred for 10 min at rt. The mixture was treated with cold (—20°C) pentane (120 mL) and washed several times with ice-cold HjO. The organic layer was dried (KjCOj) and the solvent was evaporated in vacuo. Distillation (—20°C) into a cold trap at — 78"C afforded (2-tert-butyl-l-cyclopropylidene)neopentylamine yield 1.59 g (88%) bp 80-85°C/18-20mmHg. 

Dibromoethane (311) and neopentylamine gave 1,4-dineopentylpiperazine (312) (MeOH—H2O, reflux, 40 h then NaOH reflux, 12 h 13%) ... 

W-(2,2-Dimethylcyclopropylidene)neopentylamine 10 occurs at 70 °C as a mixture of E- and Z-isomers (ratio 63 37). Its quantitative fragmentation into isobutene and neopentylisocyan-ide, either thermally by heating at 150UC or photochemically by irradiation (A > 250 nm) at 20 °C, has been well studied.4... 

Enantiomerically pure neopentylamine derivatives have been prepared from the corresponding ketones by a four-step sequence involving imine formation with (R)-a-methylbenzylamine followed by a highly diastereoselective reduction with sodium borohydride62. 

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