Hydrochloric Acid → 1-(2-Aminoethyl)-4,4-diphenylpiperidine

HRID 396618ノート

反応式

HRID 396618 の反応式
[C:1]1([C:7]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11][N:10]([CH2:13][C:14]#[N:15])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.CCOCC>C1COCC1.C(Cl)Cl>[NH2:15][CH2:14][CH2:13][N:10]1[CH2:11][CH2:12][C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9]1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 23004060(4,4-Diphenylpiperidin-1-yl)acetonitrile

生成物 1

HCID 230040551-(2-Aminoethyl)-4,4-diphenylpiperidine収率 94%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred solution of (4,4-diphenylpiperidin-1-yl)acetonitrile (3.90 g, 14.1 mmol, 1.0 equiv) in anhydrous THF (10 mL) under argon was added a solution of BH3 in THF (1.0 M, 50 mL, 50 mmol, 3.5 equiv) at room temperature. The mixture was refluxed for 4.5 hours and then cooled to room temperature and concentrated to a volume of about 30 mL. Aqueous HCl (6 N, 50 mL) was added cautiously and stirring was continued for 2 hours at 50° C. The mixture was cooled to room temperature, basified to pH 10 by addition of 6 N aq. NaOH, and extracted with CH2Cl2 (3×100 mL). The combined organic solutions were dried over MgSO4 and concentrated. To a solution of the residue in CH2Cl2 (30 mL) was added HCl in ether (1.0 M, 16 mL, 1.1 equiv). After removal of the solvents, the residue was dissolved in CH2Cl2 (10 mL) and this solution was added dropwise into ether (100 mL) with swirling. The resulting solid was filtered and washed with ether (3×50 mL). This solid was taken up in water (20 mL), which was basified to pH 10 by addition of 1 M aqueous NaOH, and extracted with CH2Cl2 (3×50 mL). The combined organic solutions were dried over MgSO4 and concentrated to give 3.70 g (94%) of white solid, which was characterized spectroscopically.

後処理

  1. temperatureThe mixture was refluxed for 4.5 hours
  2. concentrationconcentrated to a volume of about 30 mL
  3. additionAqueous HCl (6 N, 50 mL) was added cautiously
  4. temperatureThe mixture was cooled to room temperature
  5. additionbasified to pH 10 by addition of 6 N aq. NaOH
  6. extractionextracted with CH2Cl2 (3×100 mL)
  7. dry with materialThe combined organic solutions were dried over MgSO4
  8. concentrationconcentrated
  9. customAfter removal of the solvents
  10. dissolutionthe residue was dissolved in CH2Cl2 (10 mL)
  11. additionthis solution was added dropwise into ether (100 mL)
  12. filtrationThe resulting solid was filtered
  13. washwashed with ether (3×50 mL)
  14. additionwhich was basified to pH 10 by addition of 1 M aqueous NaOH
  15. extractionextracted with CH2Cl2 (3×50 mL)
  16. dry with materialThe combined organic solutions were dried over MgSO4
  17. concentrationconcentrated

出典と根拠

ORDレコード
ord-b44e1848a95a47d8a30cce4b6678310d
出典データセット
uspto-grants-2003_08
特許番号
US06608086B2

反応ノート

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