Hydrochloric Acid → 3-Amino-propyl-4,4-diphenyl piperidine

HRID 382660ノート

反応式

HRID 382660 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.Cl.[OH-].[Na+]>C1COCC1>[NH2:16][CH2:15][CH2:14][CH2:13][N:10]1[CH2:11][CH2:12][C:7]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 155128643-(4,4-Diphenylpiperidin-1-yl)propionitrile

生成物 1

HCID 101085183-Amino-propyl-4,4-diphenyl piperidine収率 66.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred solution of 3-(4,4-diphenylpiperidin-1-yl)propionitrile (2.00 g, 6.89 mmol, 1.0 equiv) in anhydrous THF (20 mL) under argon was added a solution of BH3 in THF (1.0 M, 24.1 mL, 24 mmol, 3.5 equiv) at room temperature. The mixture was refluxed for 4.5 hours and then cooled to room temperature. Aqueous HCl (6 N, 50 mL) was added and stirring was continued for 1 hour. The mixture was basified to pH 9 by addition of 6 N aq. NaOH, extracted 3 times with CH2Cl2, dried over MgSO4 and concentrated. The residue was purified by flash chromatography (SiO2, EtoAc-MeOH-isopropylamine 9:1:0 to 4:1:0.2) to give 1.35 g (66%) of tan solid, which was characterized spectroscopically.

後処理

  1. temperatureThe mixture was refluxed for 4.5 hours
  2. extractionextracted 3 times with CH2Cl2
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (SiO2, EtoAc-MeOH-isopropylamine 9:1:0 to 4:1:0.2)

出典と根拠

ORDレコード
ord-18187e0c32c240f2909c142b14444599
出典データセット
uspto-grants-2001_10
特許番号
US06310076B1

反応ノート

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