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4-Hydroxybenzoic Acid → Tert-butyl 4-{4-[(4-hydroxybenzoyl)amino]phenyl}piperazine-1-carboxylate

HRID 1459423
ノート
印刷プレビュー

反応式

HRID 1459423 の反応式
[CH3:1][C:2]([CH3:20])([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)=[O:6])[CH3:3].[OH:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=1.C1CCN(C(Cl)=[N+]2CCCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CCOC(C)=O.C(Cl)Cl>[CH3:3][C:2]([CH3:20])([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:14]=[CH:15][C:16]([NH:17][C:26](=[O:27])[C:25]3[CH:29]=[CH:30][C:22]([OH:21])=[CH:23][CH:24]=3)=[CH:18][CH:19]=2)[CH2:9][CH2:8]1)=[O:6])[CH3:1]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 1354-Hydroxybenzoic AcidHCID 81531DiisopropylethylamineHCID 11011301tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylateHCID 15429165Chlorodipiperidinocarbenium hexafluorophosphate

生成物 1

HCID 54019812Tert-butyl 4-{4-[(4-hydroxybenzoyl)amino]phenyl}piperazine-1-carboxylate収率 45.8%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To a 100 mL round bottomed flask with a stirring bar and an argon inlet was added 4-(4-(1,1-dimethylethoxycarbonyl)piperazin-1-yl)aniline (0.868 g, 3.13 mmol), 4-hydroxybenzoic acid (0.525 g, 3.80 mmol), chloro-N,N,N',N',-bis(pentamethylene)formamidinium hexafluorophosphate (1.35 g, 3.74 mmol), and CH2Cl2 (45 mL). This mixture was cooled in an ice bath and diisopropylethylamine (0.96 mL, 5.52 mmol) was added. The ice bath was allowed to expire and the mixture was stirred at ambient temperature 18 h. The mixture was diluted with EtOAc and washed with 10% aqueous citric acid, water and brine. Drying (MgSO4), filtration and removal of the solvent in vacuo gave an oil. This material was chromatographed on 100 g of silica gel using 70% EtOAc-hexane as eluant to give 0.57 g of N-(4-(4-(1,1-dimethylethoxycarbonyl)piperazin-1-yl)phenyl)-4-hydroxybenzamide as a grey solid.

後処理

  1. temperatureThis mixture was cooled in an ice bath
  2. washwashed with 10% aqueous citric acid, water and brine
  3. customDrying
  4. filtration(MgSO4), filtration and removal of the solvent in vacuo
  5. customgave an oil
  6. customThis material was chromatographed on 100 g of silica gel using 70% EtOAc-hexane as eluant

出典と根拠

ORDレコード
ord-7f744fab07174f798f01c81f3c5e0520
出典データセット
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05854245

反応ノート

読み込み中…

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