Potassium Carbonate → [1-(3-Phenylpropyl)piperidin-3-yl]methanol

HRID 1978314노트

반응식

HRID 1978314 반응식
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][OH:8])[CH2:2]1.Br[CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[C:13]1([CH2:12][CH2:11][CH2:10][N:1]2[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][OH:8])[CH2:2]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 107308Piperidin-3-ylmethanol

생성물 1

HCID 21993827[1-(3-Phenylpropyl)piperidin-3-yl]methanol

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

To a solution of 10.07 g (87.43 mM) of 3-piperidinemethanol and 19.1 g (96.2 mM) of 1-bromo-3-phenylpropane in 150 ml of acetonitrile was added 18.1 g (131 mM) of potassium carbonate and the mixture was stirred at room temperature for one day. This reaction mixture was poured in water and extracted with 3 portions of ethyl acetate. The pooled organic layer was dried over MgSO4 and the solvent was distilled off under reduced pressure to provide crude 1-(3-phenylpropan-1-yl)piperidine-3-methanol. This crude product was not purified but used as it was in the next reaction. To a solution of this crude 1-(3-phenylpropan-1-yl)piperidine-3-methanol and 14.6 ml (105 mM) of triethylamine in 150 ml of tetrahydrofuran was added a solution of 11.0 g (96.2 mM) of methanesulfonyl chloride in 50 ml of tetrahydrofuran dropwise under ice-cooling and the mixture was further stirred at the prevailing temperature for 0.5 hour. This reaction mixture was poured in water and extracted with 3 portions of ethyl acetate. The pooled organic layer was dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was dissolved in 500 ml of N,N-dimethylformamide, followed by addition of 17.8 g (96.2 mM) of potassium phthalimide, and the mixture was stirred at 100° C. overnight. This reaction mixture was poured in water and extracted with 3 portions of ethyl acetate. The pooled organic layer was dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 to ethyl acetate) to provide the title compound.

후처리

  1. extractionextracted with 3 portions of ethyl acetate
  2. dry with materialThe pooled organic layer was dried over MgSO4
  3. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-7b9419ced0dc4e44ba13488fe4bb74f8
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06235731B1

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