Phenethylamine → HCID 23587943, compound

HRID 489285Notes

Reaction equation

HRID 489285 reaction equation
[O:1]=[C:2]1[N:7]2[CH2:8][CH2:9][C:10]3[C:15]([C:6]2=[CH:5][CH:4]=[C:3]1[C:16]([OH:18])=O)=[CH:14][CH:13]=[CH:12][CH:11]=3.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[CH2:41]([NH2:49])[CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CN(C=O)C>[CH2:41]([NH:49][C:16]([C:3]1[C:2](=[O:1])[N:7]2[CH2:8][CH2:9][C:10]3[C:15]([C:6]2=[CH:5][CH:4]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:18])[CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22266462HCID 22266462, compound

Product 1

HCID 23587943HCID 23587943, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-oxo-6,7-dihydropyrido[2,1,a]isoquinoline-3-carboxylic acid (3-101-03) (76 mg) in DMF (2.0 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloric acid salt (EDC, 83 mg), 1-hydroxybenzotriazole (HOBt, 58 mg), and phenethylamine (80 mg) at room temperature. After the reaction mixture was stirred for 18 h, the reaction was quenched with 0.5 mol/L hydrochloric acid. To the reaction mixture was added ethyl acetate and the organic layer was separated. The aqueous layer was extracted three times with ethyl acetate, and the combined organic layers were washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The obtained crude crystal was recrystallized to give 4-oxo-6,7-dihydropyrido[2,1,a]isoquinoline-3-carboxylic acid phenethylamide (3-101) (84 mg, 74%) as an yellow crystal.

Workup

  1. customthe reaction was quenched with 0.5 mol/L hydrochloric acid
  2. additionTo the reaction mixture was added ethyl acetate
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted three times with ethyl acetate
  5. washthe combined organic layers were washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe obtained crude crystal
  9. customwas recrystallized

Sources & evidence

ORD record
ord-c0db24da576f49a68abf82f755031384
Source dataset
uspto-grants-2005_12
Patent number
US06977266B2

Reaction notes

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