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

HRID 382660노트

반응식

HRID 382660 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 101085183-Amino-propyl-4,4-diphenyl piperidine수율 66.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-18187e0c32c240f2909c142b14444599
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310076B1

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