Hydrochloric Acid → Methyl 4-(1-(naphthalen-1-ylsulfonyl)piperidin-2-yl)butanoate

HRID 1881684노트

반응식

HRID 1881684 반응식
[C:1]1([S:11](Cl)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]1[CH2:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26].C(N(C(C)C)C(C)C)C.Cl.[Na+].[Cl-]>C(Cl)Cl>[C:1]1([S:11]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]2[CH2:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 665601-Naphthalenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 66772062Methyl 4-(piperidin-2-yl)butanoate hydrochloride

생성물 1

HCID 57904267Methyl 4-(1-(naphthalen-1-ylsulfonyl)piperidin-2-yl)butanoate수율 65.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Naphthalene-1-sulfonyl chloride (13.7 g, 60.55 mmol) was added to a solution of methyl 4-(piperidine-2-yl)butanoate hydrochloride (2) (3.74 g, 20.2 mmol) in methylene chloride (143 ml). N-Ethyl-diisopropylamine (10.2 ml, 60.55 mmol) was then added dropwise. The reaction mixture was stirred overnight at room temperature. The completeness of the reaction was checked by means of TLC. When the reaction was complete, the reaction mixture was acidified with 1 M HCl (aqueous) and the aqueous phase was saturated with NaCl solution and then extracted 4× with methylene chloride. The combined organic phases were dried over MgSO4, filtered and concentrated under reduced pressure. Purification via column chromatography (aluminium oxide; hexane/ethyl acetate 97.3→9:1) gave the desired product methyl 4-(1-(naphthalen-1-ylsulfonyl)piperidin-2-yl)butanoate 3 (4.95 g, 65%).

후처리

  1. extractionextracted 4× with methylene chloride
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification via column chromatography (aluminium oxide; hexane/ethyl acetate 97.3→9:1)

출처 및 근거

ORD 기록
ord-872ab7a15ed2424cbe579ba2608b03ab
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318769B2

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