Dimethylformamide → 1,2-Diphenylethyl 1-methylpiperidine-4-carboxylate

HRID 1910519

反応式

HRID 1910519 の反応式
C(Cl)(=O)C(Cl)=O.Cl.[CH3:8][N:9]1[CH2:14][CH2:13][CH:12]([C:15]([OH:17])=[O:16])[CH2:11][CH2:10]1.CN(C=O)C.[C:23]1([CH:29](O)[CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH3:8][N:9]1[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:16])[CH2:11][CH2:10]1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 941781,2-DiphenylethanolHCID 27600434-Piperidinecarboxylic acid, 1-methyl-, hydrochloride (1:1)

生成物 1

HCID 709257871,2-Diphenylethyl 1-methylpiperidine-4-carboxylate収率 37%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Oxalyl dichloride (141 μl, 1.67 mmol) was added dropwise to a solution of 1-methylpiperidine-4-carboxylic acid hydrochloride (300 mg, 1.67 mmol) in DCM (20 ml) and few drops of DMF (catalytic amount). The reaction was stirred at room temperature for 2 hours. The volatiles were removed under vacuum, and the crude was taken up with pyridine (20 ml). 1,2-Diphenylethanol (331 mg, 1.67 mmol) was added, and the resulting suspension was heated under microwave irradiation at 140° C. for 1 hour. Pyridine was removed under vacuum, and the crude was purified by flash chromatography (DCM/MeOH=97/3 to 94/6) to obtain 1,2-diphenylethyl 1-methylpiperidine-4-carboxylate (200 mg).

後処理

  1. customThe volatiles were removed under vacuum
  2. temperaturethe resulting suspension was heated under microwave irradiation at 140° C. for 1 hour
  3. customPyridine was removed under vacuum
  4. customthe crude was purified by flash chromatography (DCM/MeOH=97/3 to 94/6)

出典と根拠

ORDレコード
ord-b13f5ebe1c75469c810a0348eb917fd9
出典データセット
uspto-grants-2013_12
特許番号
US08604015B2

関連ノート

読み込み中…