m-Aminoacetanilide → N-[3-[[2-[(Phenylmethyl)amino]ethyl]amino]phenyl]acetamide hydrochloride

HRID 728928Notes

Reaction equation

HRID 728928 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.Cl.[Cl:13][CH2:14][CH2:15][NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)(C)C>[ClH:13].[C:18]1([CH2:17][NH:16][CH2:15][CH2:14][NH:1][C:2]2[CH:3]=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 7604m-AminoacetanilideHCID 13054189Benzenemethanamine, N-(2-chloroethyl)-, hydrochloride (1:1)

Product 1

HCID 19755020N-[3-[[2-[(Phenylmethyl)amino]ethyl]amino]phenyl]acetamide hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

Combine N-(3-aminophenyl)acetamide (31 g, 0.206 mol) and N-(2-chloroethyl)benzenemethanamine hydrochloride (17.0 g, 0.083 mol) and heat to 180° C. for 1 h. After this time, allow to cool to approximately 85° C. and add isopropanol (100 mL) to precipitate a solid. Decant the solvent and dissolve the white residue in refluxing methanol (800 mL). Filter hot and allow the solution to cool to room temperature. After 2 h, filter the resulting white solid and wash with methanol (50 mL) to give the title compound.

Workup

  1. customto precipitate a solid
  2. customDecant the solvent
  3. dissolutiondissolve the white residue
  4. temperaturein refluxing methanol (800 mL)
  5. filtrationFilter hot
  6. temperatureto cool to room temperature
  7. filtrationfilter the resulting white solid
  8. washwash with methanol (50 mL)

Sources & evidence

ORD record
ord-451b349d08374e7391a6fb18f4aff60e
Source dataset
uspto-grants-1991_09
Patent number
US05051422

Reaction notes

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