3-Phenylpropylamine → HCID 59527268, compound

HRID 384459Notes

Reaction equation

HRID 384459 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:19][CH2:20][C:21]([OH:23])=O)[C:10]=1[CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[C:48]1([CH2:54][CH2:55][CH2:56][NH2:57])[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.C(N(CC)C(C)C)(C)C.C(=O)([O-])O.[Na+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:19][CH2:20][C:21]([NH:57][CH2:56][CH2:55][CH2:54][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:23])[C:10]=1[CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 6

HCID 162593-PhenylpropylamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59527575HCID 59527575, compound

Product 1

HCID 59527268HCID 59527268, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[4-(Benzyloxy)-3-methylquinolin-2-yl]propionic acid (213 mg) and 1-hydroxybenzotriazole hydrate (107 mg) were dissolved in DMF (4 mL). 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (140 mg), 3-phenylpropylamine (134 mg), and N,N-diisopropylethylamine (0.14 mL) were added thereto, and the mixture was stirred at room temperature for 72 hours. A saturated aqueous sodium hydrogen carbonate solution (20 mL) was added to the reaction mixture, followed by extraction with ethyl acetate (200 mL). The organic layer was washed sequentially with water and saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=30/1) to obtain 3-[4-(benzyloxy)-3-methylquinolin-2-yl]-N-(3-phenylpropyl)propanamide (90 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate (200 mL)
  2. washThe organic layer was washed sequentially with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=30/1)

Sources & evidence

ORD record
ord-27244276fcb34153bf98ef814141ab5d
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

Loading…