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

HRID 1794844Notes

Reaction equation

HRID 1794844 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[O:11]1[C:15]2([CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[O:14][CH2:13][CH2:12]1>N1C=CC=CC=1.O>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:18]1[CH2:19][CH2:20][C:15]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:16][CH2:17]1)([O-:10])=[O:9]

Participants

5

Reactant 2

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

Product 1

HCID 22220290HCID 22220290, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of 2-fluoronitrobenzene (10 g, 70.9 mmol) and 1,4-dioxa-8-aza-spiro[4.5]decane (10 g, 69.8 mmol) in pyridine (70 mL) was heated at 70° C. for 1 day, diluted with water, and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried with sodium sulfate, and filtered. The solvent was removed under reduced pressure to give the title compound (15 g) as a red oil; 1H NMR (300 MHz, CDCl3) δ 1.88 (t, J=5.6 Hz, 4 H), 3.16 (t, J=5.6 Hz, 4 H), 4.00 (s, 4 H), 7.03 (dd, J=8.2, 8.2 Hz, 2 H), 7.17 (d, J=8.2 Hz, 2 H), 7.40 (ddd, J=8.2, 8.2, 1.7 Hz, 1 H), 7.77(dd, J=8.4, 1.7 Hz, 1 H); MS (ES) m/z: 265.1 (MH+); HRMS Calcd. for C13H17N2O4(MH+): 265.1188. Found: 265.1164.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-51b0708ce1c64db19021c6c5f2f583f7
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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