1,4-Dioxa-8-azaspiro(4.5)decane → HCID 21876726, compound

HRID 1167455Notes

Reaction equation

HRID 1167455 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.C(N(CC)C(C)C)(C)C.[O:21]1[C:25]2([CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[O:24][CH2:23][CH2:22]1>C(#N)C>[O:21]1[C:25]2([CH2:30][CH2:29][N:28]([C:7]3[CH:6]=[CH:5][C:4]([N+:9]([O-:11])=[O:10])=[CH:3][C:2]=3[F:1])[CH2:27][CH2:26]2)[O:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 81531DiisopropylethylamineHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 21876726HCID 21876726, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3,4-Difluoronitrobenzene (15.53 g, 0.098 M) was dissolved in acetonitrile (150 ml), and treated with N,N-diisopropylethylamine (31.5 g, 0.244 M) and 1,4-dioxa-8-azaspiro[4,5]decane (15.36 g, 0.107 M). The mixture was stirred and heated to reflux for 18 hours. After cooling, product precipitated as a yellow solid, and was filtered off (16.1 g); further product could be obtained by concentrating the residues (8.43 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 hours
  3. temperatureAfter cooling
  4. customproduct precipitated as a yellow solid
  5. filtrationwas filtered off (16.1 g)
  6. customfurther product could be obtained
  7. concentrationby concentrating the residues (8.43 g)

Sources & evidence

ORD record
ord-4a2729c17dec436ea8b83ed01976b3d8
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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