Piperidin-4-ol → 4-((4-Hydroxypiperidin-1-yl)sulfonyl)benzaldehyde

HRID 1697086Notes

Reaction equation

HRID 1697086 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1)=[O:2].[OH:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:13][CH:14]1[CH2:19][CH2:18][N:17]([S:9]([C:6]2[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=2)(=[O:11])=[O:10])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 79341Piperidin-4-olHCID 516892Sodium BicarbonateHCID 27592104-Formylbenzene-1-sulfonyl chloride

Product 1

HCID 866248554-((4-Hydroxypiperidin-1-yl)sulfonyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-formyl-benzenesulfonyl chloride (1.0 g) in DCM (10 mL) was added 4-hydroxypiperidine (0.984 g), followed by NaHCO3 (10 mL, aq sat'd) and the mixture stirred for 2 h at RT. The aqueous layer was washed with DCM (2×25 mL), and the combined organic portions washed with brine, dried over Na2SO4, filtered, and the solvent removed under reduced pressure to provide 4-(4-hydroxypiperidine-1-sulfonyl)benzaldehyde. The product was purified on anhydrous silica (10% MeOH/DCM). M+H 269.9

Workup

  1. washThe aqueous layer was washed with DCM (2×25 mL)
  2. washthe combined organic portions washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-d4f28b959ab341d69b62e4980688dec1
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

Loading…