Acetic Acid → trans-N-cyclopropyl-2-phenylcyclohexanamine

HRID 387238

반응식

HRID 387238 반응식
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.C(O)(=O)C.[C:9]1([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]2=O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([BH3-])#N.[Na+]>CO>[CH:1]1([NH:4][C@@H:16]2[CH2:17][CH2:18][CH2:19][CH2:20][C@@H:15]2[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:3][CH2:2]1.[CH:1]1([NH:4][C@@H:16]2[CH2:17][CH2:18][CH2:19][CH2:20][C@H:15]2[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:3][CH2:2]1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 69828CyclopropylamineHCID 955922-PhenylcyclohexanoneHCID 5003444Sodium cyanoborohydride

생성물 2

HCID 68756221trans-N-cyclopropyl-2-phenylcyclohexanamine수율 44%HCID 71251557cis-N-cyclopropyl-2-phenylcyclohexanamine수율 23%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

To a cooled solution of 2.78 ml (40 mmol) of cyclopropylamine and 2.87 ml (50 mmol) of acetic acid, together with 5 g of 3 Å molecular sieves, in 50 ml of methanol, are added 3.5 g (20 mmol) of 2-phenylcyclohexanone. The reaction mixture is stirred for 3.5 hrs at reflux. The reaction mixture is then cooled to 0° C. and 3 g (50 mmol) of sodium cyanoborohydride are slowly added and the reaction mixture is further stirred for 2 hrs at reflux. The cooled reaction mixture is then filtered over a cake of diatomaceous earth. The cake is washed twice by 80 ml of methanol and the combined methanolic extracts are concentrated under vacuum. 100 ml of water are then added to the residue and the pH is ajusted to 12 with a 1 N solution of sodium hydroxyde. The watery layer is extracted with 100 ml of ethyl acetate. The organic layer is washed twice by brine and dried over magnesium sulfate to yield after concentration 3.52 g of a yellow oil. Column chromatography on silica gel (gradient heptane/ethyl acetate) yields 1.0 g (23% yield) of cis-N-cyclopropyl-2-phenylcyclo-hexanamine as a yellow oil (M+H=216) and 1.9 g (44% yield) of trans-N-cyclopropyl-2-phenylcyclohexanamine as a colorless oil (M+H=216).

후처리

  1. temperatureat reflux
  2. stirringthe reaction mixture is further stirred for 2 hrs
  3. temperatureat reflux
  4. customThe cooled reaction mixture
  5. filtrationis then filtered over a cake of diatomaceous earth
  6. washThe cake is washed twice by 80 ml of methanol
  7. concentrationthe combined methanolic extracts are concentrated under vacuum
  8. addition100 ml of water are then added to the residue
  9. extractionThe watery layer is extracted with 100 ml of ethyl acetate
  10. washThe organic layer is washed twice by brine
  11. dry with materialdried over magnesium sulfate
  12. customto yield after concentration 3.52 g of a yellow oil

출처 및 근거

ORD 기록
ord-7e0b6bdaf8034bddadbc3b14f824f930
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372982B2

연결된 노트

불러오는 중…