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

HRID 866060

反応式

HRID 866060 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e18f3390aef9413982f5ea92f102083a
出典データセット
uspto-grants-1996_10
特許番号
US05569664

関連ノート

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