p-Bromochlorobenzene → Tert-butyl 4-(4-chlorophenylamino)piperidine-1-carboxylate

HRID 856072

반응식

HRID 856072 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1.[NH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1.CC(C)([O-])C.[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:9][CH:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]2)=[CH:3][CH:4]=1

참가 물질

9

반응물 4

HCID 7806p-BromochlorobenzeneHCID 8857Ethyl AcetateHCID 12682914-Amino-1-Boc-piperidineHCID 23676156Sodium t-butoxide

생성물 1

HCID 1491503Tert-butyl 4-(4-chlorophenylamino)piperidine-1-carboxylate수율 86%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 634876Binap, (A+-)-촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

A mixture of p-bromochlorobenzene (1.91 g, 9.99 mmol), tert-butyl 4-aminopiperidine-1-carboxylate (2.0 g, 9.99 mmol), palladium acetate (45 mg, 0.2 mmol), (R)-(+)-BINAP (187 mg, 0.3 mmol) and sodium tert-butoxide (1.35 g, 14.0 mmol) in toluene (20 ml) was refluxed under a nitrogen atmosphere for 1 hour. Ethyl acetate and water were added to the reaction mixture while stirring, the insoluble substances were removed by filtration through Celite, and the filtrate was then extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1) to afford tert-butyl 4-(4-chlorophenylamino)piperidine-1-carboxylate (2.67 g, yield 86%) as a yellow powder.

후처리

  1. temperaturewas refluxed under a nitrogen atmosphere for 1 hour
  2. customthe insoluble substances were removed by filtration through Celite
  3. extractionthe filtrate was then extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1)

출처 및 근거

ORD 기록
ord-c276d8dff44d4683981ae2411bdadb15
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262212B2

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