Sodium hydride → 5-(3-(tetrahydropyran-2-yloxy)-1propyl)-10,11dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile

HRID 482231노트

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HRID 482231 반응식
[H-].[Na+].[CH:3]1[C:13]2[CH2:12][CH2:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[CH:8]([C:18]#[N:19])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[O:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[O:26][CH2:27][CH2:28][CH2:29]Br>C1(C)C=CC=CC=1>[O:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[O:26][CH2:27][CH2:28][CH2:29][C:8]1([C:18]#[N:19])[C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[CH2:11][CH2:12][C:13]2[CH:3]=[CH:4][CH:5]=[CH:6][C:7]1=2

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranHCID 1409111110,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile

생성물 1

HCID 187993365-(3-(tetrahydropyran-2-yloxy)-1propyl)-10,11dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile수율 99%

시약·촉매·용매 1

HCID 1140Toluene용매3회

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온도
50 °C

실험 절차

In a 50 ml roundbottom flask equipped with magnetical stirring, thermometer and addition funnel, sodium hydride (0.8 g, 0.02 mol, 60% dispersion in oil) was suspended in dry toluene under an atmosphere of nitrogen. A solution of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile (3.0 g 0.014 mol, prepared in a similar way as described in J. Med. Chem., 6, (1963), 251) in dry toluene (15 ml) was added. The reaction mixture was heated to reflux temperature in 30 minutes and then heated at reflux temperature for 150 minutes. After-cooling to about 50° C., a solution of 3-bromopropyl tetrahydropyranyl ether (4.5 g, 0.02 mol) in dry toluene (6 ml) was added dropwise. The reaction mixture was heated at reflux temperature for 5 h and then left stirring at room temperature overnight. After filtration of precipitated salts, the solution was washed with 1N HCl (100 ml), diluted with more toluene (100 ml) and finally washed with water. After drying (MgSO4), the organic phase was evaporated in vacuo affording 7.2 g (99%) of 5-(3-(tetrahydropyran-2-yloxy)-1propyl)-10,11dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile.

후처리

  1. customIn a 50 ml roundbottom flask equipped with magnetical stirring
  2. additionthermometer and addition funnel
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux temperature in 30 minutes
  5. temperatureheated
  6. temperatureat reflux temperature for 150 minutes
  7. temperatureThe reaction mixture was heated
  8. temperatureat reflux temperature for 5 h
  9. waitleft
  10. filtrationAfter filtration of precipitated salts
  11. washthe solution was washed with 1N HCl (100 ml)
  12. additiondiluted with more toluene (100 ml)
  13. washfinally washed with water
  14. dry with materialAfter drying (MgSO4)
  15. customthe organic phase was evaporated in vacuo

출처 및 근거

ORD 기록
ord-972105fa7d9546f58782b62d10f27b9f
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05795888

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