Benzenemethanamine, 3,4-dichloro- → HCID 15220957, compound

HRID 1608962Notes

Reaction equation

HRID 1608962 reaction equation
[N+](C1C=CC([O:10][C:11]([N:13]2[CH:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:15](=[O:30])[NH:14]2)=O)=CC=1)([O-])=O.[Cl:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[Cl:40])[CH2:35][NH2:36]>CCO>[Cl:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[Cl:40])[CH2:35][NH:36][C:11]([N:13]1[CH:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:15](=[O:30])[NH:14]1)=[O:10]

Participants

4

Reactant 2

HCID 1608Benzenemethanamine, 3,4-dichloro-HCID 15287761HCID 15287761, compound

Product 1

HCID 15220957HCID 15220957, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-[(4-nitrophenyl)oxycarbonyl]4,5-diphenyl-3-pyrazolidinone (1.00 g, 2.48 mmol) and 3,4-dichlorobenzylamine (5 mL) in 50 mL abs. EtOH was heated to reflux for 8 hours. Solvent was removed in vacuo, the residue taken up in CH2Cl2, washed twice with 1N HCl and once with pH 7 buffer, and dried over Na2SO4. After removal of solvent in vacuo, the product was purified by chromatography (0-35% EtOAc:hexane gradient) to give 250 mg (23%) solid:

Workup

  1. temperatureto reflux for 8 hours
  2. customSolvent was removed in vacuo
  3. washwashed twice with 1N HCl and once with pH 7 buffer
  4. dry with materialdried over Na2SO4
  5. customAfter removal of solvent in vacuo
  6. customthe product was purified by chromatography (0-35% EtOAc:hexane gradient)

Sources & evidence

ORD record
ord-39d7fda9499a4f5781deeae07cfd11ca
Source dataset
uspto-grants-1995_03
Patent number
US05399565

Reaction notes

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