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Water → 3-(1-(4-Chloro-2,5-dimethylphenylsulfonyl)piperidin-2-yl)propionic Acid Ethyl Ester

HRID 2388649
Notes
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Reaction equation

HRID 2388649 reaction equation
C(N(CC)CC)C.[ClH:8].[CH2:9]([O:11][C:12](=[O:21])[CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][NH:16]1)[CH3:10].Cl[C:23]1[C:24]([CH3:34])=[C:25]([S:30](Cl)(=[O:32])=[O:31])[CH:26]=[C:27]([CH3:29])[CH:28]=1.O>C(Cl)Cl>[CH2:9]([O:11][C:12](=[O:21])[CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][N:16]1[S:30]([C:25]1[CH:26]=[C:27]([CH3:29])[C:28]([Cl:8])=[CH:23][C:24]=1[CH3:34])(=[O:32])=[O:31])[CH3:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 186172913-Chloro-2,5-dimethylbenzenesulfonyl chlorideHCID 19261412Ethyl 3-(piperidin-2-yl)propanoate hydrochloride

Product 1

HCID 579162463-(1-(4-Chloro-2,5-dimethylphenylsulfonyl)piperidin-2-yl)propionic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

Triethylamine (30 g) was added dropwise to a solution of 3-(piperidin-2-yl)propionic acid ethyl ester hydrochloride (30 g) in methylene chloride (210 ml) at 0° C. and the mixture was then stirred at room temperature for 10 minutes. Chloro-2,5-dimethylbenzene-1-sulfonyl chloride (32.3 g) was then added slowly and the mixture was stirred for 2 hours. The reaction was observed by thin layer chromatography. Because of incomplete conversion, the mixture was stirred for a further 17 hours before the reaction was ended by addition of water (200 ml). The phases were separated and the aqueous phase was extracted with MC (150 ml). The combined organic phases were dried with Na2SO4, filtered and concentrated in vacuo. Purification of the crude product was carried out by chromatography on silica gel (5% ethyl acetate in hexane). The yield was 47.23 g (90%).

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. stirringBecause of incomplete conversion, the mixture was stirred for a further 17 hours before the reaction
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with MC (150 ml)
  5. dry with materialThe combined organic phases were dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude product

Sources & evidence

ORD record
ord-1440a6162b8249cabd96e8d641874358
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08268814B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes