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

HRID 2381164노트

반응식

HRID 2381164 반응식
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]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acid2회HCID 292052294-(4-Isopropyl-phenylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1caf7480eeb94f788b3ee9ab19206942
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258158B2

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