N-Methylbenzylamine → HCID 10199221, compound

HRID 1975402Notes

Reaction equation

HRID 1975402 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:10](O)(=O)/[CH:11]=[CH:12]\[C:13](O)=O>C(O)C.C(OCC)(=O)C>[CH3:1][N:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:3](=[N:2][CH2:10][C:11]1[CH:8]=[CH:7][CH:6]=[CH:13][CH:12]=1)[CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 7669N-MethylbenzylamineHCID 444266Maleic Acid

Product 1

HCID 10199221HCID 10199221, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The oily ethoxyiminium salt was combined with 7.6 mL (59 mmol) of methylbenzylamine in 70 mL of ethanol and stirred at room temperature 24 hours. It was then heated for 2 hours at 90°, cooled to 0°, and the solid amidine was filtered off. The solid was dissolved in ethyl acetate and 1 equivalent of maleic acid in ethyl acetate was added to yield 5.1 g of product as the maleate salt, mp 116-118.

Workup

  1. temperatureIt was then heated for 2 hours at 90°
  2. temperaturecooled to 0°
  3. filtrationthe solid amidine was filtered off
  4. dissolutionThe solid was dissolved in ethyl acetate

Sources & evidence

ORD record
ord-26688c820f0f4658a3ce4407b07514af
Source dataset
uspto-grants-1994_02
Patent number
US05286752

Reaction notes

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