Reaction #1787142

ord-528f1c1c2fb14619b03d9b1a7625817e

Reaction equation

O
water
O=C1CCCO1
γ-BL
CC(=O)N(C)C
DMA
→
CN1CCCC1=O
NMP
Yield 60.0%
O=C(O)CCCO
γ-hydroxybutyric acid

Reactants

O
water
—
lactones
—
secondary amines
—
N,N-dialkyl-omega-hydroxycarboxamides
O=C1CCCO1
γ-BL
CC(=O)N(C)C
DMA
—
N-alkylated lactams

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

JP-A-1 186 864 (Derwent Abstr. 89-259000/36) discloses the preparation of N-alkylated lactams by reaction of the corresponding lactones with secondary amines in the presence of water via the corresponding N,N-dialkyl-omega-hydroxycarboxamides as intermediates. According to Example 1 of this patent application, the reaction of γ-BL with aqueous DMA gives an NMP yield of 60% and additionally forms methylamides of γ-hydroxybutyric acid. In the single further example according to the application, too, an NMP yield of 60% is reported for the corresponding reaction of γ-BL with DMA.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06348601B2uspto-grants-2002_02