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

HRID 1194690

반응식

HRID 1194690 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1304b6314bb14c6dbf27df954ac43158
출처 데이터셋
uspto-grants-1989_03
특허 번호
US04816464

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