Ethanol → HCID 61113174, compound

HRID 1841957Notes

Reaction equation

HRID 1841957 reaction equation
[CH3:1][N:2]([CH3:23])[C:3]([CH:5]1[CH2:10][CH2:9][N:8]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH2:7][CH2:6]1)=[O:4].C(O)C.[Cl-].[NH4+]>[Fe].O>[CH3:1][N:2]([CH3:23])[C:3]([CH:5]1[CH2:6][CH2:7][N:8]([S:11]([C:14]2[CH:15]=[CH:16][C:17]([NH2:20])=[CH:18][CH:19]=2)(=[O:13])=[O:12])[CH2:9][CH2:10]1)=[O:4]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 67192604HCID 67192604, compound

Product 1

HCID 61113174HCID 61113174, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

1-(4-Nitro-benzenesulfonyl)-piperidine-4-carboxylic acid dimethylamide (0.17 g, 0.49 mmol) was suspended in a 5:1 mixture of ethanol and water (3 ml). To this solution was added iron powder (0.08 g, 0.98 mmol) followed by saturated ammonium chloride solution (0.1 ml) and the mixture was stirred at room temperature for 18 hours. After this time, the reaction mixture was filtered through a pad of celite, the celite was washed with ethanol (10 ml) and ethyl acetate (50 ml) and the solution was concentrated under vacuum. The resulting residue was partitioned between DCM (50 ml) and water (20 ml), the organic layer was separated, dried with MgSO4, filtered and concentrated to afford the title compound (0.15 g, 100% yield) as a yellow solid. Tr=1.71 min, m/z (ES+) (M+H)+ 312.

Workup

  1. filtrationAfter this time, the reaction mixture was filtered through a pad of celite
  2. washthe celite was washed with ethanol (10 ml) and ethyl acetate (50 ml)
  3. concentrationthe solution was concentrated under vacuum
  4. customThe resulting residue was partitioned between DCM (50 ml) and water (20 ml)
  5. customthe organic layer was separated
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7bdacfb4059e4692a22f20bddb195c8f
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

Loading…