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

HRID 1724886노트

반응식

HRID 1724886 반응식
[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

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c6de050ff7d8409a86d65613d38ab3cf
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07488827B2

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