Ammonia → 9-Aminobicyclo[3.3.1]nonane-9-carbonitrile

HRID 1040335

반응식

HRID 1040335 반응식
[C-:1]#[N:2].[Na+].[NH3:4].[NH4+].[Cl-].[CH:7]12[C:15](=O)[CH:11]([CH2:12][CH2:13][CH2:14]1)[CH2:10][CH2:9][CH2:8]2.Cl>CCO.CCOCC.O>[NH2:4][C:15]1([C:1]#[N:2])[CH:11]2[CH2:12][CH2:13][CH2:14][CH:7]1[CH2:8][CH2:9][CH2:10]2

참가 물질

9

반응물 5

HCID 222Ammonia2회HCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 86638Bicyclo(3.3.1)nonan-9-one

생성물 1

HCID 667208249-Aminobicyclo[3.3.1]nonane-9-carbonitrile수율 52.7%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 3283Diethyl Ether용매

반응 조건

온도
50 °C

실험 절차

Add successively 21 mL of water, 1.12 g (22.8 mmol) of sodium cyanide, 4.52 mL (54.27 mmol) of 12N aqueous ammonia solution and 2.32 g (43.41 mmol) of NH4Cl to a solution of 3 g (21.7 mmol) of bicyclo[3.3.1]nonan-9-one in 40 mL of EtOH. Stir the reaction mixture for 18 h at 50° C. Then add 5 mL of 12N aqueous ammonia solution and heat the mixture again for 4 h at 50° C. Cool the solution to RT then distribute in 100 mL of a 1:1 mixture of ether/1N aqueous soda solution. After extraction, wash the organic phase with 3×50 mL of water, dry over Na2SO4 and concentrate under reduced pressure. Take up the residue obtained in 50 mL of ether and then treat for 1 minute with a gentle stream of hydrogen chloride. Filter the hydrochloride thus obtained, wash with 20 mL of ether and distribute in 100 mL of a 1:1 mixture of DCM/saturated aqueous solution of Na2CO3. Extract the aqueous phase again with 50 mL of DCM, then combine the organic phases, wash with 2×20 mL of water and dry over Na2SO4. After concentration under reduced pressure, we obtain 1.88 g of 9-aminobicyclo[3.3.1]nonane-9-carbonitrile in the form of oil.

후처리

  1. temperatureheat the mixture again for 4 h at 50° C
  2. temperatureCool the solution to RT
  3. extractionAfter extraction
  4. washwash the organic phase with 3×50 mL of water
  5. dry with materialdry over Na2SO4
  6. concentrationconcentrate under reduced pressure
  7. customobtained in 50 mL of ether
  8. filtrationFilter the hydrochloride
  9. customthus obtained
  10. washwash with 20 mL of ether
  11. additiondistribute in 100 mL of a 1:1 mixture of DCM/saturated aqueous solution of Na2CO3
  12. extractionExtract the aqueous phase again with 50 mL of DCM
  13. washwash with 2×20 mL of water
  14. dry with materialdry over Na2SO4
  15. concentrationAfter concentration under reduced pressure, we

출처 및 근거

ORD 기록
ord-32b477e260094be2a2fc8596b53bcdce
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552201B2

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