Acetonitrile → 8-Octyl-1,4-dioxa-8-azaspiro[4.5]decane

HRID 1194690Notes

Reaction equation

HRID 1194690 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].C(#N)C.I[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>O>[CH2:21]([N:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 123801-IodooctaneHCID 674351,4-Dioxa-8-azaspiro(4.5)decane

Product 1

HCID 212492808-Octyl-1,4-dioxa-8-azaspiro[4.5]decaneYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 15 g (0.105 mol) of 1,4-dioxa-8-azaspiro[4.5]decane, 15.93 g (0.115 mol) of K2CO3, and 100 ml of acetonitrile is added dropwise 18.92 ml (0.105 mol) of iodooctane. The mixture is stirred overnight at room temperature and then at 65° C. for 2 hours. After cooling, the mixture was diluted with water and extracted with methylene chloride. The combined extracts are washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue is triturated with ether and filtered. The filtrate is concentrated in vacuo to yield 24.04 g (90%) of title compound as a clear oil: IR (neat) 2925 and 1094 cm-1 ; NMR (CDCl3) δ3.97 (s, 4H), 2.56 (br, 4H), 2.38 (m, 2H), 1.78 (m, 4H), 1.51 (br, 2H), 1.28 (s, 10H), 0.89 (m, 3H).

Workup

  1. waitat 65° C. for 2 hours
  2. temperatureAfter cooling
  3. extractionextracted with methylene chloride
  4. washThe combined extracts are washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue is triturated with ether
  8. filtrationfiltered
  9. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-1304b6314bb14c6dbf27df954ac43158
Source dataset
uspto-grants-1989_03
Patent number
US04816464

Reaction notes

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