Acetic Acid → 2-(3-{[1-(3-benzylquinolin-2-yl)-2-methylpropyl]amino}propyl)-1H-isoindole-1,3(2H)-dione

HRID 271826Notes

Reaction equation

HRID 271826 reaction equation
[CH2:1]([C:8]1[C:9]([CH:18]([NH2:22])[CH:19]([CH3:21])[CH3:20])=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[BH-](O[C:33](=[O:35])[CH3:34])OC(=O)C)(=O)C.[Na+].[C:37]([OH:40])(=O)[CH3:38].O>C(Cl)Cl>[CH2:1]([C:8]1[C:9]([CH:18]([NH:22][CH2:1][CH2:8][CH2:9][N:10]2[C:33](=[O:35])[C:34]3[C:38](=[CH:7][CH:2]=[CH:3][CH:4]=3)[C:37]2=[O:40])[CH:19]([CH3:20])[CH3:21])=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 598361941-(3-Benzylquinolin-2-yl)-2-methylpropan-1-amine

Product 1

HCID 598361892-(3-{[1-(3-benzylquinolin-2-yl)-2-methylpropyl]amino}propyl)-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(3-benzylquinolin-2-yl)-2-methylpropan-1-amine 15 (31 mg, 1 eq.) in CH2Cl2 (3 ml), was added aldehyde 16 (0.8 eq., 17 mg), sodium triacetoxy borohydride, and acetic acid. The reaction mixture was stirred for 3 h at room temperature. Water was added and then the aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated to yield 46 mg of 2-(3-{[1-(3-benzylquinolin-2-yl)-2-methylpropyl]amino}propyl)-1H-isoindole-1,3(2H)-dione 17.

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium bicarbonate, saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f735bcd893ba43599d4441fe7d3ed6e6
Source dataset
uspto-grants-2008_11
Patent number
US07452996B2

Reaction notes

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