Hydrochloric Acid → 4-Carbamoyl-4-(4-chloro-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 242567노트

반응식

HRID 242567 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)([C:14]#[N:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-:23].[Na+].Cl>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([C:14](=[O:23])[NH2:15])([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 49760270tert-Butyl 4-(4-chlorophenyl)-4-cyanopiperidine-1-carboxylate

생성물 1

HCID 450739964-Carbamoyl-4-(4-chloro-phenyl)-piperidine-1-carboxylic acid tert-butyl ester수율 58%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 4-(4-chloro-phenyl)-4-cyano-piperidine-1-carboxylic acid tert-butyl ester (500 mg, 1.56 mmol) in ethanol (15 ml) was added 2 ml 10 N aqueous sodium hydroxide. The resulting solution was warmed to reflux for 2 hours, cooled to room temperature, poured into 1 N aqueous hydrochloric acid, and extracted into ethyl acetate. The organic extracts were washed with brine, dried over magnesium sulfate, and concentrated in vacuo. Recovered yellow oil was purified by silica gel chromatography, eluting with dichloromethane-methanol (9.6:0.4) to give the title compound (306 mg, 58%). MS m/z: 339 (M+1)

후처리

  1. temperatureThe resulting solution was warmed
  2. temperatureto reflux for 2 hours
  3. extractionextracted into ethyl acetate
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customRecovered yellow oil
  8. customwas purified by silica gel chromatography
  9. washeluting with dichloromethane-methanol (9.6:0.4)

출처 및 근거

ORD 기록
ord-d41f3fd5741e4ab8b6c69e74c68f7264
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653096B2

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