Potassium Carbonate → 2-(3-Methoxyphenyl)-1-(2-pyridinylmethyl)pyrrolidine

HRID 233031노트

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HRID 233031 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:13][CH2:12][CH2:11][NH:10]2)[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27]Cl>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:13][CH2:12][CH2:11][N:10]2[CH2:27][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=2)[CH:6]=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 36138242-(3-Methoxyphenyl)pyrrolidine

생성물 1

HCID 233612632-(3-Methoxyphenyl)-1-(2-pyridinylmethyl)pyrrolidine수율 91%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 2-(3-methoxyphenyl)pyrrolidine (3.0 g) in dry acetonitrile (70 ml) was added milled potassium carbonate (6.1 g) followed by 2-picolyl chloride hydrochloride (3.1 g) at ambient temperature, under nitrogen, with stirring for 65 hrs. The reaction mixture was filtered through a pad of celite, and the filter cake was washed with ethyl acetate. The combined filtrates were concentrated and the residue was purified by flash column chromatography (silica gel, 5% methanol/ether). The appropriate fractions were collected and concentrated to give 4.1 g (91%) of 2-(3-methoxyphenyl)-1-(2-pyridinylmethyl)pyrrolidine. 2-(3-Methoxyphenyl)-1-(2-pyridinylmethyl)pyrrolidine and 48% hydrobromic acid (40 ml) were warmed to 100° C. for 7 hrs, cooled to ambient temperature, and neutralized with saturated sodium bicarbonate solution. The mixture was extracted with dichloromethane (2 times). The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by flash column chromatography (silica gel, 1:1 ethyl acetate/dichloromethane). The appropriate fractions were collected and concentrated to give 2.7 g (69%) of product, mp 96°-98° C.

후처리

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washthe filter cake was washed with ethyl acetate
  3. concentrationThe combined filtrates were concentrated
  4. customthe residue was purified by flash column chromatography (silica gel, 5% methanol/ether)
  5. customThe appropriate fractions were collected
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-abe4dc7be5dd4f3c986db96eb8435d7e
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05591856

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