1-Phenethylamine, (+)- → HCID 178461968, compound

HRID 1602284Notes

Reaction equation

HRID 1602284 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:13]([C:14]#[N:15])=[C:12]([N:16]=[CH:17][N:18](C)C)[NH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[C:21]1([C@H:27](N)[CH3:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:13]3[C:12](=[N:16][CH:17]=[N:18][C:14]=3[NH:15][C@@H:27]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH3:28])[NH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6431891-Phenethylamine, (+)-HCID 178484265HCID 178484265, compound

Product 1

HCID 178461968HCID 178461968, compound

Conditions

Temperature
120 °C

Procedure

Under a nitrogen atmosphere, a mixture of 1.5 g (5.19 mmol) of 3-(3-chloro-phenylamino)-4-cyano-5-(dimethylamino-methyleneamino)-pyrazole (Step 49.2) and 10 ml of (R)-1-phenylethylamine is stirred at 120° C. for 40 hours and then concentrated by evaporation under a HV. The oily residue is purified by flash chromatography on silica gel having a particle size of 0.04-0.06 mm using ethyl acetate/hexane (7:3). The product-containing fractions are concentrated by evaporation and the resinous residue is dissolved in a mixture of 5 ml of ethanol and 1.4 ml of 4N hydrochloric acid. Concentration by evaporation again and recrystallization of the residue from ethanol/diethyl ether and from ethanol yield the title compound; m.p. 150-152° C.; EI-MS: (M)+ =364; [a]D20 =-233.7±2.1° (c=0.486% methanol).

Workup

  1. concentrationconcentrated by evaporation under a HV
  2. customThe oily residue is purified by flash chromatography on silica gel having a particle size of 0.04-0.06 mm
  3. concentrationThe product-containing fractions are concentrated by evaporation
  4. dissolutionthe resinous residue is dissolved in a mixture of 5 ml of ethanol and 1.4 ml of 4N hydrochloric acid
  5. concentrationConcentration
  6. customby evaporation again
  7. customrecrystallization of the residue from ethanol/diethyl ether

Sources & evidence

ORD record
ord-a328c17297ee4e6faaf309a46f6ca448
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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