1,1'-Carbonyldiimidazole → N-[2-(3,4-Dichlorophenyl)-2-(4-hydroxy-4-phenyl-piperidino)ethyl]-N-methyl-3,5-bis(trifluoromethyl)phenylacetamide hydrochloride salt

HRID 609865ノート

反応式

HRID 609865 の反応式
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH2:13][C:14]([OH:16])=O)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:31][C:32]1[CH:33]=[C:34]([CH:39]([N:43]2[CH2:48][CH2:47][C:46]([OH:55])([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[CH2:45][CH2:44]2)[CH2:40][NH:41][CH3:42])[CH:35]=[CH:36][C:37]=1[Cl:38]>O1CCCC1>[ClH:31].[Cl:31][C:32]1[CH:33]=[C:34]([CH:39]([N:43]2[CH2:44][CH2:45][C:46]([OH:55])([C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)[CH2:47][CH2:48]2)[CH2:40][N:41]([CH3:42])[C:14](=[O:16])[CH2:13][C:5]2[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=[C:3]([C:2]([F:17])([F:18])[F:1])[CH:4]=2)[CH:35]=[CH:36][C:37]=1[Cl:38]

参加物

5

反応物 3

HCID 682631,1'-CarbonyldiimidazoleHCID 1235873,5-Bis(trifluoromethyl)phenylacetic acidHCID 15434904HCID 15434904、化合物

生成物 1

HCID 22129658N-[2-(3,4-Dichlorophenyl)-2-(4-hydroxy-4-phenyl-piperidino)ethyl]-N-methyl-3,5-bis(trifluoromethyl)phenylacetamide hydrochloride salt収率 48%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
23 °C

実験手順

A solution of 3,5-bis(trifluoromethyl)phenylacetic acid (1.61 g) and 1,1'-carbonyldiimidazole (1.01 g) in tetrahydrofuran (15 mL) was stirred at reflux for 0.5 hours. The reaction was cooled to 23° C. and treated with a solution of N-[2-(3,4-dichlorophenyl)-2-(4-hydroxy-4-phenylpiperdino)ethyl]methylamine (2.24 g) in tetrahydrofuran (70 mL). The reaction was stirred at 23° C. for 18 hours. The reaction was evaporated to an oil, and the oil was partitioned between diethylether and 1N hydrochloric acid (100 mL). The organic layer was treated with etheral hydrochloric acid to produce the title compound as a white solid (950 mg); mp 230° C.; MS: m/z=633(M+1); NMR: 1.73 (m,2), 2.42 (m,1), 2.75 (m,1), 3.01 (s,4), 3.86 (m,4,), 4.43 (m,1), 4.85 (m,1), 5.34 (m,1), 7.34 (m,5), 7.73 (s2), 7.87 (m,5), 8.06 (s,1), 11.36 (broad s,1). Analysis Calculated: C, 53.79; H, 4.36; N, 4.18; Found: C, 54.06; H, 4.48; N, 4.23.

後処理

  1. temperatureat reflux for 0.5 hours
  2. customThe reaction was evaporated to an oil
  3. customthe oil was partitioned between diethylether and 1N hydrochloric acid (100 mL)
  4. additionThe organic layer was treated with etheral hydrochloric acid

出典と根拠

ORDレコード
ord-62388616b5514758bb0b21a6dbd8050f
出典データセット
uspto-grants-1999_12
特許番号
US05998444

反応ノート

読み込み中…