Chloroacetonitrile → 6-Fluoro-3-(1-cyanomethyl-4-piperidyl)-1,2-benzisoxazole

HRID 233940

반응식

HRID 233940 반응식
[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:24][C:25]#[N:26]>C(#N)C>[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:24][C:25]#[N:26])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

참가 물질

5

반응물 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole

생성물 1

HCID 130783426-Fluoro-3-(1-cyanomethyl-4-piperidyl)-1,2-benzisoxazole

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (11 g, 50 mmol), K2CO3 (8.5 g, 61.6 mmol) and 2-chloroacetonitrile (5.5 g, 73 mmol) in acetonitrile (250 ml) was heated at reflux for 24 hours. The in,solubles were filtered off and rinsed with methylene chloride (DCM). During concentration of the solvents on the rotary evaporator, crystals appeared. The crystals were collected and weighed 5.79 g. The product in the mother liquor was further purified by flash chromatography over a silica gel column (SiO2, 70 g; eluted with DCM, and 1% CH3OH in DCM). The second crop of product thus obtained weighed 5.2 g. The total yield was 10.9 g. The sample was recrystallized once more form ethanol, m.p. 130°-132° C.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. filtrationThe in,solubles were filtered off
  4. washrinsed with methylene chloride (DCM)
  5. customDuring concentration of the solvents on the rotary evaporator, crystals
  6. customThe crystals were collected
  7. customThe product in the mother liquor was further purified by flash chromatography over a silica gel column (SiO2, 70 g; eluted with DCM, and 1% CH3OH in DCM)
  8. customThe second crop of product thus obtained
  9. customThe sample was recrystallized once more form ethanol, m.p. 130°-132° C.

출처 및 근거

ORD 기록
ord-43a542def3a44b06aa0868ef65c614c5
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05593995

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