Acetonitrile → HCID 21273621, compound

HRID 329926Notes

Reaction equation

HRID 329926 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[O:10]1[C:14]2([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[O:13][CH2:12][CH2:11]1.C([O-])([O-])=O.[K+].[K+].C(#N)C>O.C(OCC)C>[O:10]1[C:14]2([CH2:19][CH2:18][N:17]([C:8]3[CH:9]=[CH:2][CH:3]=[CH:4][C:5]=3[C:6]#[N:7])[CH2:16][CH2:15]2)[O:13][CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 674351,4-Dioxa-8-azaspiro(4.5)decane

Product 1

HCID 21273621HCID 21273621, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 10 g (0.0825 mol) p-fluorobenzonitrile, 47 g (0.3282 mol) of 1,4-dioxa-8-azaspiro[4.5]decane, 17 g (0.123 mol) of K2CO3, and 100 ml of acetonitrile is stirred at 90°-100° C. for three days. The reaction mixture is allowed to cool to ambient temperature, diluted with water and extracted with methylene chloride. The combined extracts are washed with brine, dried over Na2SO4, and concentrated in vacuo to give a pasty solid. Trituration with ethyl ether furnishes 13.4 g (67%) of title compound: m.p. 134°-135° C.; IR (KBr) 2210 and 1600 cm-1 ; NMR (CDCl3) δ 7.48 (d, 2H), 6.88 (d, 2H), 4.0 (s, 4H), 3.58-3.40 (m, 4H), and 1.90-1.70 (m, 4H).

Workup

  1. extractionextracted with methylene chloride
  2. washThe combined extracts are washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give a pasty solid

Sources & evidence

ORD record
ord-1f4bdcfc29b5478bbca5e1c13da86c15
Source dataset
uspto-grants-1990_01
Patent number
US04894374

Reaction notes

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