Sodium hydride → 3-Methyl-1-(3-piperidin-1-yl-propyl)-4-(3-trifluoromethoxy-phenyl)-piperazin-2-one

HRID 1096252

반응식

HRID 1096252 반응식
[H-].[Na+].[CH3:3][CH:4]1[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]([F:20])([F:19])[F:18])[CH:11]=2)[CH2:8][CH2:7][NH:6][C:5]1=[O:21].Cl[CH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.Cl.ClCCCN1CCCCC1>CC(N(C)C)=O.C1(C)C=CC=CC=1>[CH3:3][CH:4]1[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]([F:20])([F:19])[F:18])[CH:11]=2)[CH2:8][CH2:7][N:6]([CH2:23][CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[C:5]1=[O:21]

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 79624N-(3-chloropropyl)piperidine hydrochlorideHCID 79625Piperidine, 1-(3-chloropropyl)-HCID 667830063-Methyl-4-(3-trifluoromethoxy-phenyl)-piperazin-2-one

생성물 1

HCID 591592633-Methyl-1-(3-piperidin-1-yl-propyl)-4-(3-trifluoromethoxy-phenyl)-piperazin-2-one수율 84%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 31374Dimethylacetamide용매

반응 조건

온도
75 °C

실험 절차

NaH (55% dispersion in mineral oil, 36 mg, 0.82 mmol) was added portionwise at RT to a solution of 3-methyl-4-(3-trifluoromethoxy-phenyl)-piperazin-2-one (150 mg, 0.55 mmol) in DMA (3 mL), then after 1 h a solution of 1-(3-chloropropyl)-piperidine in toluene [prepared from commercially available 1-(3-chloropropyl)-piperidine hydrochloride (542 mg, 2.74 mmol) by partitioning between toluene (4 ml) and 1 M aq. sodium hydroxide solution (4 ml) and drying of the organic layer with MgSO4] was added. The reaction mixture was heated at 75° C. for 1 h, then partitioned between sat. aq. NaHCO3 solution and CH2Cl2. The organic layer was dried (MgSO4), filtered, and evaporated. Chromatography (IST Isolute® Flash NH2; EtOAc) afforded the title compound (184 mg, 84%). Light yellow oil, MS: 400.3 (M+H)+.

후처리

  1. customby partitioning between toluene (4 ml) and 1 M aq. sodium hydroxide solution (4 ml)
  2. dry with materialdrying of the organic layer with MgSO4]
  3. additionwas added
  4. custompartitioned between sat. aq. NaHCO3 solution and CH2Cl2
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

출처 및 근거

ORD 기록
ord-8d3832cdf33643f0b02bc38948c8353f
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138175B2

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