Sodium Hydroxide → HCID 67038217, compound

HRID 604934Notes

Reaction equation

HRID 604934 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:20]=[CH:19][C:9]([O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:3].[OH:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>CN(C)C=O.C(O)(=O)C>[CH3:1][S:2]([NH:5][C:6]1[CH:20]=[CH:19][C:9]([O:10][C:11]2[CH:18]=[CH:17][C:14]([CH2:15][N:25]3[CH2:26][CH2:27][CH:22]([OH:21])[CH2:23][CH2:24]3)=[CH:13][CH:12]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 79341Piperidin-4-olHCID 5049666Sodium triacetoxyborohydrideHCID 22135779HCID 22135779, compound

Product 1

HCID 67038217HCID 67038217, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(4-methylsulfonylaminophenoxy)benzaldehyde (2.50 g) in dimethyl formamide (25 mL) were added 4-hydroxypiperidine (1.74 g) and acetic acid (2.5 mL), and the solution was stirred. To the reaction solution was added sodium triacetoxyborohydride (2.18 g) and the solution was stirred for 2 days. After finishing the reaction, the reaction solution was neutralized with 2N aqueous solution of sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (methylene chloride:methanol=10:1) to give the title compound (1.90 g) having the following physical data.

Workup

  1. stirringthe solution was stirred for 2 days
  2. customthe reaction
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe obtained residue was purified by column chromatography on silica gel (methylene chloride:methanol=10:1)

Sources & evidence

ORD record
ord-48ffba16f05c4d1c95a98a17021d7c90
Source dataset
uspto-grants-2011_03
Patent number
US07910741B2

Reaction notes

Loading…