3-[(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)methyl]cyclohexanone → 1-[(3-Phenyl-3-cyclohexenyl)methyl]-4-phenyl-1,2,3,6-tetrahydropyridine

HRID 1654685노트

반응식

HRID 1654685 반응식
[C:1]1([C:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH:14]3[CH2:19][CH2:18][CH2:17][C:16](=O)[CH2:15]3)[CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]1([Mg]Br)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCCC1>[C:1]1([C:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH:14]3[CH2:19][CH2:18][CH:17]=[C:16]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:15]3)[CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

4

반응물 2

HCID 117778783-[(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)methyl]cyclohexanoneHCID 178418255HCID 178418255, 화합물

생성물 1

HCID 104492741-[(3-Phenyl-3-cyclohexenyl)methyl]-4-phenyl-1,2,3,6-tetrahydropyridine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3-[(3,6-dihydro-4-phenyl-1(2H) -pyridinyl)methyl]cyclohexanone (Example A) (5.9 g) in 400 mL of tetrahydrofuran is added a solution of phenylmagnesium bromide (9.13 mL, 3.0M in diethyl ether), dropwise under nitrogen, at 0° C. The mixture is stirred at room temperature for 1 hour, then cooled in an ice bath and quenched with 250 mL of 10% aqueous hydrochloric acid solution. The solvent is evaporated in vacuo and the residue partitioned into chloroform/5% aqueous ammonium hydroxide solution. The organic extract is dried over magnesium sulfate and filtered. The filtrate is treated with trifluoroacetic acid (4.2 mL) and stirred overnight at room temperature. The solvent is evaporated in vacuo, and the residue is partitioned into ethyl acetate/5% aqueous ammonium hydroxide solution. The organic extract is dried over magnesium sulfate, filtered, and concentrated. The crude product is purified by medium pressure chromatography to give 3.9 g of (±)-1,2,3,6-tetrahydro-4-phenyl-1-[(3-phenyl-3-cyclohexen-1-yl)methyl]pyridine; mp 90°-95° C. as an off-white solid (Example 1) and 2.7 g of (±)-1,2,3,6-tetrahydro-4-phenyl-1-[(3-phenyl-2-cyclohexen-1-yl) methyl]pyridine; mp 124°-126° C. as a tan solid (Example 1a).

후처리

  1. customat 0° C
  2. temperaturecooled in an ice bath
  3. customquenched with 250 mL of 10% aqueous hydrochloric acid solution
  4. customThe solvent is evaporated in vacuo
  5. customthe residue partitioned into chloroform/5% aqueous ammonium hydroxide solution
  6. extractionThe organic extract
  7. dry with materialis dried over magnesium sulfate
  8. filtrationfiltered
  9. additionThe filtrate is treated with trifluoroacetic acid (4.2 mL)
  10. stirringstirred overnight at room temperature
  11. customThe solvent is evaporated in vacuo
  12. customthe residue is partitioned into ethyl acetate/5% aqueous ammonium hydroxide solution
  13. extractionThe organic extract
  14. dry with materialis dried over magnesium sulfate
  15. filtrationfiltered
  16. concentrationconcentrated
  17. customThe crude product is purified by medium pressure chromatography

출처 및 근거

ORD 기록
ord-4e6ceb591aba4dc8bb1ad834e2dcbeed
출처 데이터셋
uspto-grants-1995_04
특허 번호
US05409931

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