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1-Methylpiperazine → 1-(2-Chloropyridin-4-YL)-4-methylpiperazine

HRID 885950
ノート
印刷プレビュー

反応式

HRID 885950 の反応式
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][N:3]=1.[CH3:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.[Cl-].[Cl-].[Fe+2].[Pd+2]>[Cl:1][C:2]1[CH:7]=[C:6]([N:13]2[CH2:14][CH2:15][N:10]([CH3:9])[CH2:11][CH2:12]2)[CH:5]=[CH:4][N:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 531671-MethylpiperazineHCID 15165112-Chloro-4-iodopyridineHCID 23676156Sodium t-butoxide

生成物 1

HCID 722188991-(2-Chloropyridin-4-YL)-4-methylpiperazine収率 77%

試薬・触媒・溶媒 2

HCID 53384307Dichloro[1,1'-bis(di-tert-butylphosphino)ferrocene]palladium(II)触媒
HCID 1140
Toluene
溶媒

反応条件

温度
115 °C

実験手順

To a mixture of 2-chloro-4-iodopyridine (300 mg, 1.24 mmol) in toluene (4 mL) was added 1-methylpiperazine (0.14 mL, 1.24 mmol), sodium tert-butoxide (239 mg, 2.44 mmol), [1,1′-bis(di-tert-butylphosphino)ferrocene]palladium(II) dichloride (30 mg, 10% wt) and the suspension was heated to 115° C. under microwave irradiation for 30 minutes. The resulting mixture was concentrated in vacuo and partitioned between DCM (50 mL) and water (50 mL). The organic phase was washed with brine (50 mL), dried (MgSO4), and evaporated in vacuo to give the title compound (200 mg, 77%) as a brown oil. LCMS (ES+) 212.0 (M+H)+, RT 1.78 minutes (70% purity) (Method 2).

後処理

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. custompartitioned between DCM (50 mL) and water (50 mL)
  3. washThe organic phase was washed with brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

出典と根拠

ORDレコード
ord-36642310d6664144b76b5f68ff44f51e
出典データセット
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08242116B2

反応ノート

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