HCID 10801994, compound → HCID 10444326, compound

HRID 863461Notes

Reaction equation

HRID 863461 reaction equation
[CH2:1]([N:8]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[C:2]1([CH2:1][N:8]([CH3:9])[CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 10801994HCID 10801994, compound

Product 1

HCID 10444326HCID 10444326, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of N-benzyl-N-methyl[2-(4-nitrophenyl)ethyl]amine (3.9 g, 14.4 mmol) in 85% acetic acid (250 ml) was added in one portion zinc dust (9.4 g, 144 mmol). The reaction was stirred for 30 minutes, filtered, and concentrated. The residue was dissolved in water (50 ml), the solution basified with 2.5N aqueous sodium hydroxide and the mixture extracted with several portions of methylene chloride. The combined organic layers were dried over magnesium sulfate, filtered and concentrated to yield 4-(2-((phenylmethyl)(methyl)amino)ethyl)phenylamine (3.41 g, 98%). The dihydrochloride salt, from methanol-ethyl acetate, melted at 275° C. (dec).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in water (50 ml)
  4. extractionthe mixture extracted with several portions of methylene chloride
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-96b51ed1214a4f45b5f35a34cdd75dfd
Source dataset
uspto-grants-1998_02
Patent number
US05721247

Reaction notes

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