Sodium Hydroxide → 3-Azaspiro(5.5)undecane-2,4-dione

HRID 130580Notes

Reaction equation

C[O-].[Na+].C[C:5](C)(C([O-])=O)[C:6]([O-])=[O:7].[C:13]1(=[C:19](C#N)[C:20]([NH2:22])=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[OH-].[Na+]>CO>[O:7]=[C:6]1[NH:22][C:20](=[O:21])[CH2:19][C:13]2([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[CH2:5]1

Participants

Conditions

Temperature: 25 °C

Procedure

204 ml of a 5.4 M solution of sodium methylate in methanol, 550 ml methanol and 145.5 g of dimethylmalonate are placed in a 2 litre flask equipped with a mechanical stirrer, thermometer and condenser, under nitrogen flow. After 30 minutes, 148 g of cyclohexylidenecyanoacetamide are added over a period of 30 minutes. The mixture is left under agitation for 1.5 hours at 30° C., after which 626 g of 15% NaOH are added, then heated under reflux for 1.5 hours. 400 ml of methanol are distilled and the mixture is acidified with 36% HCl to pH 3 then heated under reflux for 3 hours. By cooling to 25° C. a precipitate is formed which is filtered off, washed with water until the washing waters are neutral and dried under vacuum at 45° C. 69 g of 2,4-dioxo-3-azaspiro[5,5]undecane are obtained.

Workup

customequipped with a mechanical stirrer
waitThe mixture is left under agitation for 1.5 hours at 30° C.
temperatureheated
temperatureunder reflux for 1.5 hours
distillation400 ml of methanol are distilled
temperaturethen heated
temperatureunder reflux for 3 hours
customis formed which
filtrationis filtered off
washwashed with water until the washing waters
customdried under vacuum at 45° C

Sources & evidence

ORD record: ord-e3e7d17f70c64acd86c5bd807d5391cf
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07381823B2

Reaction notes

Loading…