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Ethyl Bromide → N-(3,4-Dichlorophenyl)-1-{[(3R)-1-ethylpiperidin-3-yl]methyl}piperidine-4-carboxamide

HRID 2371191
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HRID 2371191 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]3[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[K+].[K+].[CH2:31](Br)[CH3:32]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([CH:12]2[CH2:13][CH2:14][N:15]([CH2:18][C@@H:19]3[CH2:24][CH2:23][CH2:22][N:21]([CH2:31][CH3:32])[CH2:20]3)[CH2:16][CH2:17]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]
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참가 물질

5

반응물 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 57656947N-(3,4-dichlorophenyl)-1-[(3R)-piperidin-3-ylmethyl]piperidine-4-carboxamide

생성물 1

HCID 11632679N-(3,4-Dichlorophenyl)-1-{[(3R)-1-ethylpiperidin-3-yl]methyl}piperidine-4-carboxamide수율 74%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of N-(3,4-dichlorophenyl)-1-[(3R)-piperidin-3-ylmethyl]piperidine-4-carboxamide (100 mg), potassium carbonate (41 mg) and ethyl bromide (0.022 mL) in dimethylformamide (4 ml) was stirred at room temperature for 24 hours. The reaction mixture was partitioned between dichloromethane and water. The organic layer was separated, dried over magnesium sulfate and evaporated. The residue was purified by silica column chromatography, eluting with a gradient of 0 to 10% 7M NH3/MeOH in dichloromethane to give the title compound as a white solid (80 mg, 74%).

후처리

  1. customThe reaction mixture was partitioned between dichloromethane and water
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by silica column chromatography
  6. washeluting with a gradient of 0 to 10% 7M NH3/MeOH in dichloromethane

출처 및 근거

ORD 기록
ord-a3a803a19eb94fc1a1bc9626945ad59d
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08710224B2

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