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

HRID 559354노트

반응식

HRID 559354 반응식
[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]

참가 물질

7

반응물 3

HCID 24758Sodium hydrideHCID 79625Piperidine, 1-(3-chloropropyl)-HCID 630791914-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-3-methyl-piperazin-2-one2회

생성물 2

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 31374Dimethylacetamide용매

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온도
50 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-c5d983ccb3404383a6a857c9d146e19c
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063042B2

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