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

HRID 856072

反応式

HRID 856072 の反応式
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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 634876Binap, (A+-)-触媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c276d8dff44d4683981ae2411bdadb15
出典データセット
uspto-grants-2007_08
特許番号
US07262212B2

関連ノート

読み込み中…