Trifluoroacetic acid → Piperidine-4-carboxylic acid (4-isopropyl-phenyl)-amide

HRID 2381164ノート

反応式

HRID 2381164 の反応式
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:25])[NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:22]([C:19]1[CH:18]=[CH:17][C:16]([NH:15][C:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[O:25])=[CH:21][CH:20]=1)([CH3:24])[CH3:23]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acid2 回HCID 292052294-(4-Isopropyl-phenylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 18071890Piperidine-4-carboxylic acid (4-isopropyl-phenyl)-amide収率 83.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

4-(4-Isopropyl-phenylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester (1.68 g) was dissolved in methylene chloride (50 ml), trifluoroacetic acid (2.75 g) was added at 0° C. and under an argon atmosphere and the mixture was stirred for 12 h at RT. Further trifluoroacetic acid (1.1 g) was added and stirring was continued for 1.5 h to complete the reaction. The reaction mixture was partitioned between methylene chloride and aqueous 1M NaOH, the layers were separated and the aqueous layer washed with 2M aqueous KHCO3 then dried over Na2SO4. The solvent was evaporated off, the residue was triturated with diethyl ether/heptane to give the desired piperidine-4-carboxylic acid (4-isopropyl-phenyl)-amide (1 g) as a white solid that was directly used in the next step.

後処理

  1. stirringstirring
  2. waitwas continued for 1.5 h
  3. customthe reaction
  4. customThe reaction mixture was partitioned between methylene chloride and aqueous 1M NaOH
  5. customthe layers were separated
  6. washthe aqueous layer washed with 2M aqueous KHCO3
  7. dry with materialthen dried over Na2SO4
  8. customThe solvent was evaporated off
  9. customthe residue was triturated with diethyl ether/heptane

出典と根拠

ORDレコード
ord-1caf7480eeb94f788b3ee9ab19206942
出典データセット
uspto-grants-2012_09
特許番号
US08258158B2

反応ノート

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