Acetonitrile → 8-(4-(Methylsulfonyl)phenyl)-1,4-dioxa-8-azaspiro[4.5]decane

HRID 329927

Reaction equation

HRID 329927 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](F)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C([O-])([O-])=O.[K+].[K+].[O:18]1[C:22]2([CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[O:21][CH2:20][CH2:19]1.C(#N)C>O>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:25]2[CH2:26][CH2:27][C:22]3([O:21][CH2:20][CH2:19][O:18]3)[CH2:23][CH2:24]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 679941-Fluoro-4-(methylsulphonyl)benzene

Product 1

HCID 42563608-(4-(Methylsulfonyl)phenyl)-1,4-dioxa-8-azaspiro[4.5]decaneYield 77.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10 g (0.057 mol) of p-fluorophenyl methyl sulfone, 8.72 g (0.063 mol) of K2CO3, 24.66 g (0.172 mol) of 1,4-dioxa-8-azaspiro[4.5]-decane and 50 ml of acetonitrile is stirred overnight at 90°-100° C. After cooling, the mixture is diluted with water and extracted with methylene chloride. The combined extracts are washed with brine, dried over Na2SO4, and concentrated in vacuo. Trituration with ethyl ether affords 13.11 g (77%) of title compound as a white solid: m.p. 192°-194° C.; IR (KBr) 1588, 1369, and 1290 cm-1 ; NMR (CDCl3) δ 7.74 (m, 2H), 6.96 (m, 2H), 4.02 (s, 4H), 3.54 (m, 4H), 3.03 (s, 3H), and 1.81 (m, 4H).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with methylene chloride
  3. washThe combined extracts are washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7a0af4ea29a74a42902eadeffd979f2f
Source dataset
uspto-grants-1990_01
Patent number
US04894374

Linked notes

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