Triethylamine → 4-Nitrophenyl 3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethoxy)phenyl]piperidine-1-carboxylate

HRID 876235ノート

反応式

HRID 876235 の反応式
[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][NH:14][CH2:13][CH:12]([NH:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:11]2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:34](Cl)(=[O:45])[O:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1.C(=O)(O)[O-].[Na+]>ClCCl.O>[C:18]1([C:17]([NH:16][CH:12]2[CH2:11][CH:10]([C:7]3[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:25])[F:26])=[CH:9][CH:8]=3)[CH2:15][N:14]([C:34]([O:35][C:36]3[CH:37]=[CH:38][C:39]([N+:42]([O-:44])=[O:43])=[CH:40][CH:41]=3)=[O:45])[CH2:13]2)=[O:24])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 516892Sodium BicarbonateHCID 66701272N-{5-[4-(trifluoromethoxy)phenyl]piperidin-3-yl}benzamide

生成物 1

HCID 667012994-Nitrophenyl 3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethoxy)phenyl]piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

At 0° C., 200 mg (0.55 mmol) of N-{5-[4-(trifluoromethoxy)phenyl]piperidin-3-yl}benzamide and 153 μl (1 l mmol) of triethylamine were initially charged in 17 ml of dichloromethane, and 111 mg (0.55 mmol) of 4-nitrophenyl chlorocarbonate were added slowly. The mixture was stirred at 0° C. for 2 h and then warmed to RT. Water and saturated aqueous sodium bicarbonate solution were added, and the reaction mixture was extracted. The organic phase was dried over sodium sulphate and concentrated under reduced pressure. The crude product was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 254 mg (87% of theory)

後処理

  1. temperaturewarmed to RT
  2. extractionthe reaction mixture was extracted
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient)

出典と根拠

ORDレコード
ord-c19d8255e5eb45bc857d6a87472ed558
出典データセット
uspto-grants-2015_03
特許番号
US08987248B2

反応ノート

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