Ethanol → HCID 10068550, compound

HRID 1252077Notes

Reaction equation

HRID 1252077 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[N:21]=[C:22]([NH:25][C:26](=[O:29])[CH2:27][CH3:28])[S:23][CH:24]=2)[CH2:15][CH2:14]1)([O-])=O.C(O)C.[Cl-].[NH4+]>O.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH:13]1[CH2:14][CH2:15][N:16]([CH2:19][C:20]2[N:21]=[C:22]([NH:25][C:26](=[O:29])[CH2:27][CH3:28])[S:23][CH:24]=2)[CH2:17][CH2:18]1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 10431891HCID 10431891, compound

Product 1

HCID 10068550HCID 10068550, compoundYield 71.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-[4-(5-nitro-3-indolyl)piperidinomethyl]-2-propionylaminothiazole (1.39 g) and ethanol (60 ml) was added to a solution of ammonium chloride (1.08 g) in water (20 ml), followed by stirring at 80° C. Iron (1.13 g) was added thereto and the mixture was refluxed for 2 hours, after which it was filtered. The residue was washed with hot ethanol and the filtrate and washings were combined and concentrated under reduced pressure. The residue was made alkaline to litmus paper with 2N aqueous sodium hydroxide solution and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and elution was carried out with a mixture of chloroform and methanol to give 4-[4-(5-amino-3-indolyl)piperidinomethyl]-2-propionylaminothiazole (0.92 g).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. filtrationafter which it was filtered
  3. washThe residue was washed with hot ethanol
  4. concentrationconcentrated under reduced pressure
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. washThe residue was subjected to column chromatography on silica gel and elution
  10. additionwas carried out with a mixture of chloroform and methanol

Sources & evidence

ORD record
ord-7c448c6884ce4984b96ec3d648cecf40
Source dataset
uspto-grants-1988_05
Patent number
US04742057

Reaction notes

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