Acetone → Ethyl 1-(2-chloroethyl)piperidine-4-carboxylate

HRID 533778ノート

反応式

HRID 533778 の反応式
[NH:1]1[CH2:11][CH2:10][CH2:9][CH:3](C(OCC)=O)[CH2:2]1.Br[CH2:13][CH2:14][Cl:15].[C:16]([O-:19])([O-])=[O:17].[K+].[K+].[CH3:22][C:23](C)=O>>[Cl:15][CH2:14][CH2:13][N:1]1[CH2:2][CH2:3][CH:9]([C:16]([O:19][CH2:22][CH3:23])=[O:17])[CH2:10][CH2:11]1

参加物

5

反応物 4

HCID 180AcetoneHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 98969Ethyl nipecotate

生成物 1

HCID 61287119Ethyl 1-(2-chloroethyl)piperidine-4-carboxylate収率 38.6%

実験手順

To a solution of ethyl nipecotate (20.0 mL, 130 mmol) in acetone (180 mL) was added 1-bromo-2-chloroethane (21.6 mL, 260 mmol) followed by anhydrous K2CO3 (27.12 g, 196 mmol). The reaction mixture was stirred for 24 h and then concentrated under vacuum. The resulting residue was treated with H2O (75 mL) and extracted with Et2O. The combined organic layers were dried with MgSO4, filtered, and concentrated under vacuum. Purification of the crude residue by flash chromatography (50% Et2O/50% hexane) on silica gel gave the title compound (10.99 g, 38.6%). EI-MS m/z 220(M+H+) Rt (1.20 min).

後処理

  1. concentrationconcentrated under vacuum
  2. additionThe resulting residue was treated with H2O (75 mL)
  3. extractionextracted with Et2O
  4. dry with materialThe combined organic layers were dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customPurification of the crude residue by flash chromatography (50% Et2O/50% hexane) on silica gel

出典と根拠

ORDレコード
ord-4f9cd186fef64a0f9f35f76399c2a664
出典データセット
uspto-grants-2014_10
特許番号
US08853404B2

反応ノート

読み込み中…