Tetrahydrofuran → (1-Methyl-4-piperidinyl)[3-[2-(3-fluorophenyl)ethyl]-2-pyridinyl]methanone

HRID 2351565노트

반응식

HRID 2351565 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[C:11]([C:16]#N)=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:18][N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]1[Mg]Cl.C1C[O:30]CC1>>[CH3:18][N:19]1[CH2:24][CH2:23][CH:22]([C:16]([C:11]2[C:10]([CH2:9][CH2:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[CH:15][CH:14]=[CH:13][N:12]=2)=[O:30])[CH2:21][CH2:20]1

참가 물질

4

반응물 3

HCID 8028TetrahydrofuranHCID 147168143-[2-(3-Fluorophenyl)ethyl]-2-pyridinecarbonitrileHCID 178480302HCID 178480302, 화합물

생성물 1

HCID 14716815(1-Methyl-4-piperidinyl)[3-[2-(3-fluorophenyl)ethyl]-2-pyridinyl]methanone

실험 절차

To a solution of 3-[2-(3-fluorophenyl)ethyl]-2pyridine carbonitrile (28.0 o, 0.123 mole) in 150 mL of dry THF is added 92 mL (1.48 moles/liter, 0.136 mole) of N-methylpiperidyl magnesium chloride over 10 minutes maintaining the temperature at 45°-50° C. The reaction is maintained at 40° C. to 50° C. for another 10 minutes and at ambient temperature for 45 minutes. The reaction is quenched to below pH 2 with aqueous hydrochloric acid and the resulting solution is stirred at 25° C. for 1 hour. The pH of the solution is adjusted to about 8, the oroduct is extracted with ethyl acetate, and the solution is concentrated to a residue. Following purification by silica gel chromatography, 38.3 g of product is obtained as a brown oil.

후처리

  1. temperaturemaintaining the temperature at 45°-50° C
  2. customThe reaction is quenched to below pH 2 with aqueous hydrochloric acid
  3. extractionthe oroduct is extracted with ethyl acetate
  4. concentrationthe solution is concentrated to a residue
  5. custompurification by silica gel chromatography

출처 및 근거

ORD 기록
ord-59f9a50b5ded41f39629a33d0bceecb8
출처 데이터셋
uspto-grants-1989_10
특허 번호
US04873335

반응 노트

불러오는 중…