Methanol → HCID 14998804, compound

HRID 1588982Notes

Reaction equation

HRID 1588982 reaction equation
[N+:1]([C:4]1[CH:30]=[CH:29][C:7]([O:8][CH2:9][CH:10]2[CH2:15][N:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:13][CH2:12][N:11]2[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:6][CH:5]=1)([O-])=O.CO.[Sn].[OH-].[Na+]>O.C(OCC)(=O)C>[C:16]1([N:14]2[CH2:13][CH2:12][N:11]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:10]([CH2:9][O:8][C:7]3[CH:6]=[CH:5][C:4]([NH2:1])=[CH:30][CH:29]=3)[CH2:15]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 5352426Tin atom2×HCID 14998803HCID 14998803, compound

Product 1

HCID 14998804HCID 14998804, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 2-[(4-nitrophenoxy)methyl]-4-phenyl-1-(phenylmethyl)piperazine (7.15 g, 17.7 mmol) in a 1/1 mixture of methanol and ethyl acetate (350 mL) and add tin II chloride dihydrate (20.0 g, 88.6 mmol). Stir the mixture and heat the reaction to reflux. Monitor the progress of the reaction by thin-layer chromatography and add more tin II chloride dihydrate as needed. Upon completion of the reaction, pour reaction mixture into water (200 mL) and add 4N sodium hydroxide to pH=12. Extract with a solution of ethyl acetate/methanol (2/1) (2×200 mL). Wash the combined extracts with water (200 mL) and remove the solvent in vacuo. Flash chromatograph the residue on flash silica gel (250 g) with an ethyl acetate/hexanes [gradient (1/1-1/0)] to give the title compound.

Workup

  1. temperatureheat
  2. customthe reaction
  3. temperatureto reflux
  4. customMonitor the progress of the reaction by thin-layer chromatography
  5. customUpon completion of the reaction
  6. additionpour
  7. extractionExtract with a solution of ethyl acetate/methanol (2/1) (2×200 mL)
  8. washWash the combined extracts with water (200 mL)
  9. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-78b22254b30448099351f413120ea0a3
Source dataset
uspto-grants-1993_06
Patent number
US05223623

Reaction notes

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