Hexane → [1-[2-(4-Methoxyphenyl)ethyl]-4-piperidinyl]methanone

HRID 1165210

반응식

HRID 1165210 반응식
FC1C=CC(CN2C3C=CC=CC=3N=C2)=CC=1.CCCCCC.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][N:34]2[CH2:39][CH2:38][CH:37]([C:40](OC)=[O:41])[CH2:36][CH2:35]2)=[CH:28][CH:27]=1>C1COCC1>[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][N:34]2[CH2:39][CH2:38][CH:37]([CH:40]=[O:41])[CH2:36][CH2:35]2)=[CH:28][CH:27]=1

참가 물질

5

반응물 3

HCID 8058HexaneHCID 7555721-[(4-fluorophenyl)methyl]-1H-1,3-benzodiazoleHCID 108695871-[2-(4-Methoxyphenyl)ethyl]-4-piperidinecarboxylic acid, methyl ester

생성물 1

HCID 53767224[1-[2-(4-Methoxyphenyl)ethyl]-4-piperidinyl]methanone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred, -78° C., solution of 1-[(4-fluorophenyl)methyl]-1H-benzimidazol (1.13 g, 5.00×10-3 mole) and dry THF (12 ml) under argon was added a 2.5 molar hexane solution of n-butyl ithium (2.1 ml, 5.25×10-3 mole). After 15-20 minutes at -78° C., a solution of 1-[2-(4-methoxyphenyl)ethyl]-4-piperidinecarboxylic acid, methyl ester (1.39 g, 5.01×10-3 mole) and dry THF (6 ml) was added dropwise via syringe. After 5-10 minutes, the cooling bath was removed and the reaction was allowed to warm. After ca. 30 minutes, the reaction was quenched by the addition of saturated aqueous NH4Cl. The reaction was transferred to a separatory funnel where the aqueous mixture was extracted two times with ethyl acetate. The ethyl acetate extracts were combined, washed with saturated aqueous NaCl, and dried over anhydrous Na2SO4. The drying agent was removed by filtration and the filtrate was evaporated at reduced pressure affording a viscous oil. This was purified by a combination of flash chromatography (ethyl acetate) and crystallization (cyclohexane) affording 1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]methanone as off white matted needles: 0.90 g (38%), m.p. 109°-111° C.

후처리

  1. waitAfter 5-10 minutes
  2. customthe cooling bath was removed
  3. temperatureto warm
  4. waitAfter ca. 30 minutes
  5. customthe reaction was quenched by the addition of saturated aqueous NH4Cl
  6. customThe reaction was transferred to a separatory funnel
  7. extractionwhere the aqueous mixture was extracted two times with ethyl acetate
  8. washwashed with saturated aqueous NaCl
  9. dry with materialdried over anhydrous Na2SO4
  10. customThe drying agent was removed by filtration
  11. customthe filtrate was evaporated at reduced pressure
  12. customaffording a viscous oil
  13. customThis was purified by a combination of flash chromatography (ethyl acetate) and crystallization (cyclohexane)

출처 및 근거

ORD 기록
ord-21da7227ebca418984c7e8df4b9248f5
출처 데이터셋
uspto-grants-1990_03
특허 번호
US04908372

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