Propionitrile → 1-(4,4,6-Trimethyl-5,6-dihydro-4H-1,3-oxazin-2-yl)but-1-en-2-amine

To a solution of 11.0 mmoles of lithium diisopropylamide (11.1 g diisopropylamine; 50 mL of 2.4 M n-butyl lithium in n-hexane) in 100 mL THF, kept at 78° C. under a nitrogen atmosphere, was added a solution of 5,6-dihydro-4,4,6-trimethyl-4H-1,3-oxazine (14.1 g; 0.10 mole) in 100 mL THF. The reaction mixture was then allowed to stir at -78° for 2 additional hours at which time a solution of propionitrile (8.3 g; 0.15 mole) in 50 mL THF was added. The reaction mixture was allowed to warm to room temperature and was quenched with 75 mL saturated NH4Cl solution. A 100 mL portion of ether was added, the organic layer was separated, washed with brine, and dried (K2CO3). After the K2CO3 was removed by filtration, the filtrate was concentrated in vacuo to give 21.2 g of a yellow liquid which was distilled to yield 15.5 g (79% yield) of product as a pale yellow oil, b.p. 140° C. at 4 mm Hg.

1. customkept at 78° C. under a nitrogen atmosphere
2. additionwas added
3. customwas quenched with 75 mL saturated NH4Cl solution
4. additionA 100 mL portion of ether was added
5. customthe organic layer was separated
6. washwashed with brine
7. dry with materialdried (K2CO3)
8. customAfter the K2CO3 was removed by filtration
9. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-190fb461a48d44f281a8d09a819a3f2d

Source dataset

uspto-grants-1983_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04414213