Toluene → Benzyl 4-(2-(dimethylamino)-2-oxoethoxy)piperidine-1-carboxylate

HRID 1091762노트

반응식

HRID 1091762 반응식
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.Cl[CH2:19][C:20]([N:22]([CH3:24])[CH3:23])=[O:21].C1(C)C=CC=CC=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:23][N:22]([CH3:24])[C:20](=[O:21])[CH2:19][O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:6][CH2:7]1

참가 물질

7

반응물 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 758862-chloro-N,N-dimethylacetamideHCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylate

생성물 1

HCID 57791803Benzyl 4-(2-(dimethylamino)-2-oxoethoxy)piperidine-1-carboxylate수율 88.1%

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 962Water용매

반응 조건

온도
25 °C

실험 절차

Benzyl 4-hydroxypiperidine-1-carboxylate (5 g, 21.25 mmol), tetrabutylammonium hydrogensulfate (0.361 g, 1.06 mmol) and 2-chloro-N,N-dimethylacetamide (4.13 g, 27.63 mmol) were added to toluene (50 mL) to this was added sodium hydroxide (21 g, 210.02 mmol) in water (30 mL) and the reaction was stirred at 25° C. overnight. The reaction mixture was quenched with water (100 mL), extracted with Et2O (3×75 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford the desired compound as an orange liquid (6.00 g, 88% yield); 1H NMR (400.132 MHz, CDCl3) δ 1.65-1.55 (2H, m), 1.93-1.86 (2H, m), 2.95 (3H, s), 3.03 (3H, s), 3.25-3.18 (2H, m), 3.63-3.57 (1H, m), 3.85-3.79 (2H, m), 4.17 (2H, s), 5.12 (2H, s), 7.38-7.30 (5H, m).

후처리

  1. customThe reaction mixture was quenched with water (100 mL)
  2. extractionextracted with Et2O (3×75 mL)
  3. dry with materialthe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

출처 및 근거

ORD 기록
ord-e753dd91363d42ad809fdc46c4ef484c
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129380B2

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