1,4-Dioxa-8-azaspiro(4.5)decane → HCID 22220290, compound

HRID 842769Notes

Reaction equation

HRID 842769 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH2:11]1[O:20][C:14]2([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[O:13][CH2:12]1>C1COCC1>[CH2:11]1[O:20][C:14]2([CH2:19][CH2:18][N:17]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[N+:8]([O-:10])=[O:9])[CH2:16][CH2:15]2)[O:13][CH2:12]1

Participants

4

Reactant 2

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 22220290HCID 22220290, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-fluoro-2-nitrobenzene (5.80 g, 41.1 mmol) and 4-piperidone ethylene ketal (6.68 g, 46.6 mmol) in THF (100 mL) was stirred at room temperature (2 h). The resulting mixture was washed with water and sodium bicarbonate solution. The aqueous layer was extracted with two portions of ethyl acetate and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. Flash chromatography on silica gel (10% ethyl acetate/hexane) afforded the title compound (7).

Workup

  1. washThe resulting mixture was washed with water and sodium bicarbonate solution
  2. extractionThe aqueous layer was extracted with two portions of ethyl acetate
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1493041b5a2241eab151f99b99a46b08
Source dataset
uspto-grants-2002_04
Patent number
US06376503B1

Reaction notes

Loading…