HCID 18940865, compound → HCID 18940839, compound

HRID 355995Notes

Reaction equation

HRID 355995 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][C:13]1[CH2:14][N:15]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=2)[CH2:16][CH2:17][CH:18]=1>Cl.[Fe]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][C:13]1[CH2:14][N:15]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=2)[CH2:16][CH2:17][CH:18]=1

Participants

4

Reactant 1

HCID 18940865HCID 18940865, compound

Product 1

HCID 18940839HCID 18940839, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolvent

Procedure

Iron powder (0.97 g; 0.0174) was added to a suspension of the compound of Description 8 [5-methoxy-3-[N-(2-(4-nitro-phenyl)-ethyl)-1,2,5,6-tetrahydro-pyridin-3-ylmethyl]-1H-indole] (1.36 g; 0.0035 mol) in 10% aqueous hydrochloric acid (70 ml). The reaction mixture was refluxed for 3 hours. The reaction mixture was then cool down to room temperature and quenched with a saturated solution of aqueous sodium carbonate. The resulting mixture was filtered through diatomaceous earth (Celite(R)), washed with water and extracted with methylene chloride. The organic extract was dried (MgSO4) and evaporated under vacuum. After purification by Flash Chromatography on silica gel using as eluent methylene chloride/methanol/ammonia (95/5/0.5), the title compound was obtained as a yellow solid (0.2 g).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. customquenched with a saturated solution of aqueous sodium carbonate
  3. filtrationThe resulting mixture was filtered through diatomaceous earth (Celite(R))
  4. washwashed with water
  5. extractionextracted with methylene chloride
  6. extractionThe organic extract
  7. dry with materialwas dried (MgSO4)
  8. customevaporated under vacuum
  9. customAfter purification by Flash Chromatography on silica gel using as eluent methylene chloride/methanol/ammonia (95/5/0.5)

Sources & evidence

ORD record
ord-e0dd66d97eb74f4e95c48ff6359e04d7
Source dataset
uspto-grants-1998_11
Patent number
US05834493

Reaction notes

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