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

HRID 1881684Notes

Reaction equation

HRID 1881684 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-872ab7a15ed2424cbe579ba2608b03ab
Source dataset
uspto-grants-2012_11
Patent number
US08318769B2

Reaction notes

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