Ethanol → HCID 56954946, compound

HRID 1841933Notes

Reaction equation

HRID 1841933 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][S:18]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[Cl-].[NH4+]>[Fe].O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][S:18]([C:21]2[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 67195158HCID 67195158, compound

Product 1

HCID 56954946HCID 56954946, compoundYield 107%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

4-(4-Nitro-benzenesulfonylamino)-piperidine-1-carboxylic acid benzyl ester (0.98 g, 2.4 mmol) was suspended in a 5:1 mixture of ethanol and water (30 ml). To this solution was added iron powder (0.34 g, 6.1 mmol) followed by saturated ammonium chloride solution (1 ml) and the mixture was heated to 80° C. for three hours. After this time, the reaction mixture was cooled to room temperature and 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 (1 g, 100% yield) as a brown solid. Tr=1.80 min, m/z (ES+) (M+H)+ 390.

Workup

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

Sources & evidence

ORD record
ord-2b385321640d4775b14324cc71dbd5ca
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

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