Hydrochloric Acid → 1-(3-Aminopropyl)-4,4-dicyclohexylpiperidine

HRID 322145ノート

反応式

HRID 322145 の反応式
[C:1]1([C:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]#[N:16])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H].Cl.CCOCC.[OH-].[Na+]>CCO.O.[Pd]>[NH2:16][CH2:15][CH2:14][CH2:13][N:10]1[CH2:11][CH2:12][C:7]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:8][CH2:9]1

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 155128643-(4,4-Diphenylpiperidin-1-yl)propionitrileHCID 178418361HCID 178418361、化合物

生成物 1

HCID 230041131-(3-Aminopropyl)-4,4-dicyclohexylpiperidine収率 61%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

A solution of 3-(4,4-diphenylpiperidin-1-yl)propionitrile (1.01 g, 3.48 mmol, 1.00 equiv) in denatured EtOH (50 mL, 5% isopropanol) was stirred at 120-130° C. in the presence of 10% Pd on activated carbon (1.00 g, Aldrich) and hydrogen at 440 psi for 15 hours. The catalyst was filtered out by use of Celite and washed with CH2Cl2 (100 mL) and MeOH (150 mL). After removal of the solvents, the residue was dissolved in CH2Cl2 (10 mL) and treated with HCl in ether (1.0M., 8.7 mmol, 2.5 equiv). The solvents were removed again and the residue was recrystallized from hot EtOH-ether (1:2). The white solid obtained from filtration of this mixture was taken up in water (40 mL), which was basified to pH 10 by addition of 1N NaOH and extracted with CH2Cl2 (3×75 mL). The combined organic solutions were dried over MgSO4 and concentrated to afford 650 mg of colorless oil (61%), which was characterized spectroscopically.

後処理

  1. filtrationThe catalyst was filtered out by use of Celite
  2. washwashed with CH2Cl2 (100 mL) and MeOH (150 mL)
  3. customAfter removal of the solvents
  4. dissolutionthe residue was dissolved in CH2Cl2 (10 mL)
  5. customThe solvents were removed again
  6. customthe residue was recrystallized from hot EtOH-ether (1:2)
  7. customThe white solid obtained from filtration of this mixture
  8. extractionextracted with CH2Cl2 (3×75 mL)
  9. dry with materialThe combined organic solutions were dried over MgSO4
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-a43396ec388b4a6280f4c2082b43fbad
出典データセット
uspto-grants-2001_04
特許番号
US06211198B1

反応ノート

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