Methylamine → HCID 54965987, compound

HRID 1429661Notes

Reaction equation

HRID 1429661 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:5][N:6]1[CH2:11][CH2:10][C:9](=O)[CH2:8][CH2:7]1.S1C=CC=C1.[CH3:22][NH2:23].[H][H]>[Pd].CO>[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([NH:23][CH3:22])[CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 8030ThiopheneHCID 23218604HCID 23218604, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54965987HCID 54965987, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of D4 (5.4 g, 24 mmol), thiophene solution (4% in diisopropylether; 2 ml), methylamine solution (40% in water, 10 ml) and 10% palladium on carbon (2 g) in methanol (150 ml) were hydrogenated at atmospheric pressure and temperature until 1 eq. (˜600 ml) of hydrogen had been taken up. After this period, the reaction mixture was filtered and the filtrate evaporated in vacuo. The crude product was purified by column chromatography (silica; 5%-10% ammonia in methanol/dichloromethane) to give D5 (4.7 g, 81%). C13H18F2N2 requires 240; Found 241 (MH+)

Workup

  1. waitAfter this period
  2. filtrationthe reaction mixture was filtered
  3. customthe filtrate evaporated in vacuo
  4. customThe crude product was purified by column chromatography (silica; 5%-10% ammonia in methanol/dichloromethane)

Sources & evidence

ORD record
ord-8fafb6609754459aa8e53b8264098888
Source dataset
uspto-grants-2015_01
Patent number
US08940743B2

Reaction notes

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