Hydrochloric Acid → 4-(3,4-Dichloro-benzenesulfonyl)-piperidine

HRID 1868031Notes

Reaction equation

HRID 1868031 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([CH:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.C([O-])([O-])=O.[Na+].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 68550800Tert-butyl 4-[(3,4-dichlorophenyl)sulfonyl]piperidine-1-carboxylate

Product 1

HCID 223974994-(3,4-Dichloro-benzenesulfonyl)-piperidineYield 79.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the sulfone from Step 7C (3.09 g, 7.8 mmol), MeOH (21 mL), and 5N HCl (4.5 mL) was heated to reflux for 1.5 h. The mixture was cooled to room temperature and sat. Na2CO3 solution (80 mL) was added. The mixture was extracted with CH2Cl2 (2×100 mL). The organic phase washed with H2O and brine, dried (MgSO4) and concentrated to afford the amine (1.82 g), a white foam, in 79% yield.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 h
  3. extractionThe mixture was extracted with CH2Cl2 (2×100 mL)
  4. washThe organic phase washed with H2O and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-432e23b2e5314003886ac50bc41be741
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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