Acetonitrile → 4-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)benzonitrile

HRID 1253318Notes

Reaction equation

HRID 1253318 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.CCOCC>[O:10]1[C:14]2([CH2:19][CH2:18][N:17]([C:2]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=3)[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 127174404-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)benzonitrileYield 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 ether furnishes 13.4 g (67%) of title compound: 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-4341de3c7ee44efa86914d554fc5972f
Source dataset
uspto-grants-1988_05
Patent number
US04748246

Reaction notes

Loading…