Sodium hydride → 4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-3-methyl-1-(3-piperidin-1-yl-propyl)-piperazin-2-one

HRID 559354ノート

反応式

HRID 559354 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6](/[CH:11]=[CH:12]/[C:13]([N:15]2[CH2:20][CH2:19][NH:18][C:17](=[O:21])[CH:16]2[CH3:22])=[O:14])[CH:7]=[CH:8][C:9]=1[Cl:10].[Cl:23][CH2:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>CN(C)C(=O)C.C1(C)C=CC=CC=1>[CH2:9]([Cl:10])[Cl:23].[CH3:13][OH:14].[NH4+:15].[OH-:14].[Cl:3][C:4]1[CH:5]=[C:6](/[CH:11]=[CH:12]/[C:13]([N:15]2[CH2:20][CH2:19][N:18]([CH2:24][CH2:25][CH2:26][N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[C:17](=[O:21])[CH:16]2[CH3:22])=[O:14])[CH:7]=[CH:8][C:9]=1[Cl:10]

参加物

7

反応物 3

HCID 24758Sodium hydrideHCID 79625Piperidine, 1-(3-chloropropyl)-HCID 630791914-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-3-methyl-piperazin-2-one2 回

生成物 2

HCID 21896990Dichloromethane methanol ammonium hydroxideHCID 575503894-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-3-methyl-1-(3-piperidin-1-yl-propyl)-piperazin-2-one収率 47%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
50 °C

実験手順

Sodium hydride (55% dispersion in mineral oil, 21 mg, 0.48 mmol) was added at room temperature to a solution of 4-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-3-methyl-piperazin-2-one (intermediate 1; 100 mg, 0.32 mmol) in N,N-dimethylacetamide (2 ml), then after 20 min a solution of 1-(3-chloropropyl)-piperidine (prepared from the commercially available hydrochloride salt (127 mg, 0.64 mmol) by basic extraction as described in intermediate 6) in toluene (1 ml) was added. The reaction mixture was stirred for 16 h at 50° C., then partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2; CH2Cl2/MeOH/NH4OH 95:5:0.25) afforded the title compound (66 mg, 47%). Colorless gum, MS (ISP)=438.4 (M+H)+.

後処理

  1. additionwas added
  2. custompartitioned between water and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

出典と根拠

ORDレコード
ord-c5d983ccb3404383a6a857c9d146e19c
出典データセット
uspto-grants-2011_11
特許番号
US08063042B2

反応ノート

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