Water → Benzyl 4-(4-(chloromethyl)pyridin-2-yl)piperazine-1-carboxylate

HRID 517560ノート

反応式

HRID 517560 の反応式
O1CCCCC1O[CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([N:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:22])[CH2:17][CH2:16]2)[CH:10]=1.S(Cl)([Cl:33])=O.O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:33][CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([N:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:22])[CH2:17][CH2:16]2)[CH:10]=1

参加物

6

反応物 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 86711499benzyl 4-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-2-yl)piperazine-1-carboxylate

生成物 1

HCID 86711500Benzyl 4-(4-(chloromethyl)pyridin-2-yl)piperazine-1-carboxylate収率 82%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of benzyl 4-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-2-yl)piperazine-1-carboxylate (7.3 g, 17.7 mmol) in DCM (30 mL), thionyl chloride (7.7 mL, 106.6 mmol) was added slowly at RT, followed by the addition of H2O (0.05 mL). The mixture was stirred at RT overnight, poured into a solution of aqueous NaHCO3 (sat., 50 mL), and extracted with DCM (2×30 mL). The combined organic layers were washed with H2O (50 mL) and brine (20 mL), dried over Na2SO4, filtered, and concentrated to afford the crude product, which was purified by silica gel column chromatography (Petroleum ether:EtOAc=3:1) to give benzyl 4-(4-(chloromethyl)pyridin-2-yl)piperazine-1-carboxylate as a yellow solid (5.0 g, 82%). MS (ES+) C18H20ClN3O2 requires: 345, found: 346 [M+H]+.

後処理

  1. extractionextracted with DCM (2×30 mL)
  2. washThe combined organic layers were washed with H2O (50 mL) and brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford the crude product, which
  7. customwas purified by silica gel column chromatography (Petroleum ether:EtOAc=3:1)

出典と根拠

ORDレコード
ord-9cfdcba404f049d4a1eb7c895fafdf2f
出典データセット
uspto-grants-2015_08
特許番号
US09115120B2

反応ノート

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