Methylamine → Ro 22-9194

HRID 329436Notes

Reaction equation

HRID 329436 reaction equation
[ClH:1].[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[N:10]([CH2:26][CH2:27][CH2:28][C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1)[C:11](=[O:25])[CH:12]([CH3:24])[N:13]1C(=O)C2C(=CC=CC=2)C1=O.CN.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>CN(C)C=O.O>[ClH:1].[ClH:1].[NH2:13][CH:12]([CH3:24])[C:11]([N:10]([C:4]1[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:3]=1[CH3:2])[CH2:26][CH2:27][CH2:28][C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1)=[O:25]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 19872168HCID 19872168, compound

Product 1

HCID 129209Ro 22-9194Yield 128.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 45.0 g of rac-2,3-dihydro-N-(2,6-dimethylphenyl)-alpha-methyl-1,3-dioxo-N-[3-(3-pyridinyl) -propyl]-1H-isoindole-2-acetamide hydrochloride dissolved in 200 ml of dimethylformamide was added 100 ml of 40% aqueous methylamine. The reaction mixture was stirred overnight, diluted with water, and extracted twice with dichloromethane. The combined organic layers were washed with water, dried with potassium carbonate, and evaporated to give an oil. The oil was converted to the dihydrochloride salt and crystallized from methanol ether to give 23.25 g of rac.-2-amino-N-(2,6-dimethylphenyl)-N-[3-(3-pyridinyl) -propyl]propanamide dihydrochloride, mp 256°-260° C. The mother liquors afforded an additional 4.9 g, mp 256°-259° C.

Workup

  1. extractionextracted twice with dichloromethane
  2. washThe combined organic layers were washed with water
  3. dry with materialdried with potassium carbonate
  4. customevaporated
  5. customto give an oil
  6. customcrystallized from methanol ether

Sources & evidence

ORD record
ord-17eabbb9f7f044a6a21070f848d2c1a5
Source dataset
uspto-grants-1990_01
Patent number
US04891429

Reaction notes

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