Pyridine → N-(3-chloro-4-methoxyphenylcarbonyl)-4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine

HRID 1683839

반응식

HRID 1683839 반응식
[F:1][C:2]([F:30])([F:29])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=2)([OH:17])[CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:6][CH:5]=1.N1C=CC=CC=1.[Cl:37][C:38]1[CH:39]=[C:40]([CH:44]=[CH:45][C:46]=1[O:47][CH3:48])[C:41](Cl)=[O:42]>O1CCCC1>[Cl:37][C:38]1[CH:39]=[C:40]([C:41]([N:14]2[CH2:15][CH2:16][CH:11]([C:10]([C:7]3[CH:6]=[CH:5][C:4]([O:3][C:2]([F:29])([F:1])[F:30])=[CH:9][CH:8]=3)([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:26])[F:27])=[CH:20][CH:19]=3)[OH:17])[CH2:12][CH2:13]2)=[O:42])[CH:44]=[CH:45][C:46]=1[O:47][CH3:48]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 47692993-Chloro-4-methoxybenzoyl chlorideHCID 190409264-[Bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine

생성물 1

HCID 19040922N-(3-chloro-4-methoxyphenylcarbonyl)-4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

In a separate reaction vessel, a solution of 0.5 gram (0.0012 mole) of 4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine (prepared in Step B of Example 7) and 0.09 gram (0.0012 mole) of pyridine in a small amount of tetrahydrofuran was stirred, and the solution of 3-chloro-4-methoxybenzoyl chloride in tetrahydrofuran, prepared above, was added. Upon completion of addition, the reaction mixture was stirred at ambient temperature for about 15 minutes and then filtered to remove a white solid. The filtrate was stirred for about 18 hours and then was partitioned between ethyl acetate and an aqueous solution saturated with sodium chloride. The organic layer was separated and passed through a column of silica gel. Elution was accomplished with 50% ethyl acetate in hexane. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.62 gram of N-(3-chloro-4-methoxyphenylcarbonyl)-4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine. The NMR spectrum was consistent with the proposed structure.

후처리

  1. customIn a separate reaction vessel
  2. additionwas added
  3. additionUpon completion of addition
  4. filtrationfiltered
  5. customto remove a white solid
  6. stirringThe filtrate was stirred for about 18 hours
  7. customwas partitioned between ethyl acetate
  8. customThe organic layer was separated
  9. washElution
  10. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-44dc4ca3cad84db4b0d21a10c2d87875
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05639763

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