Hydrochloric Acid → HCID 46193228, compound

HRID 1699410Notes

Reaction equation

HRID 1699410 reaction equation
[CH2:1]([N:8]([CH2:20][C@@H:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[OH:22])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>CO.[Fe]>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][N:8]([CH2:20][C@@H:21]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[OH:22])[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 46193227HCID 46193227, compound

Product 1

HCID 46193228HCID 46193228, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

To a solution of 13.4 g of (R)-2-[N-benzyl-N-[2-(4-nitrophenyl)ethyl]amino]-1-phenylethanol in 150 ml of methanol were added 8.6 g of iron powder and 40 ml of a 2N aqueous hydrochloric acid solution. The reaction mixture was heated to reflux for two hours, a 1N aqueous solution of sodium hydroxide was added thereto, and the insoluble matters thus produced were filtered off using Celite. The filtrate was concentrated in vacuo to remove the methanol. The resulting aqueous phase was extracted with chloroform, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated in vacuo. The resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=1/1) to give 11.45 g of (R)-2-[N-[2-(4-amino-phenyl)ethyl]-N-benzylamino]-1-phenylethanol.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for two hours
  3. customthe insoluble matters thus produced
  4. filtrationwere filtered off
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto remove the methanol
  7. extractionThe resulting aqueous phase was extracted with chloroform
  8. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated in vacuo
  10. customThe resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-4650d2e663ae4464b321394cd817d3d6
Source dataset
uspto-grants-2002_02
Patent number
US06346532B1

Reaction notes

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