Hydrazine → HCID 21936680, compound

Temperature

80 °C

To a suspension of the above 2-(1,4-dioxa-8-aza-spiro[4.5]dec-7-ylmethyl)-isoindole-1,3-dione (3.85 mmol) in absolute ethanol (25 ml) was added hydrazine (0.36 ml, 11.55 mmol). The reaction was stirred at 80° C. (oil bath) for 6 h., then cooled to ambient temperature and stirred for an additional 12 h. The thick precipitate was filtered off and washed with ethanol. The filtrate was concentrated in vacuo and reconstituted in dichloromethane (20 ml), forming a small amount of a second precipitate which was filtered off. The filtrate was evaporated in vacuo and the resulting oil was dissolved in water (10 ml) and basified with 1N sodium hydroxide until pH=10. The aqueous layer was extracted with 20% isopropyl alcohol/chloroform (12×40 ml). The combined organic extracts were dried (K2CO3), filtered and the solvent evaporated in vacuo affording 0.42 g (63%) of (1,4-dioxa-8-aza-spiro[4.5]dec-7-yl)methylamine as an oil.

1. temperaturecooled to ambient temperature
2. stirringstirred for an additional 12 h
3. filtrationThe thick precipitate was filtered off
4. washwashed with ethanol
5. concentrationThe filtrate was concentrated in vacuo
6. customforming a small amount of a second precipitate which
7. filtrationwas filtered off
8. customThe filtrate was evaporated in vacuo
9. dissolutionthe resulting oil was dissolved in water (10 ml)
10. extractionThe aqueous layer was extracted with 20% isopropyl alcohol/chloroform (12×40 ml)
11. dry with materialThe combined organic extracts were dried (K2CO3)
12. filtrationfiltered
13. customthe solvent evaporated in vacuo

ORD record

ord-f91bcc1db4e9425f82149c57fa7df15c

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07115624B1