Acetic Acid → 3-((3,5-bis(trifluoromethyl)benzylamino)methyl)-N,N-bis(cyclopropylmethyl)-8-methylquinolin-2-amine

HRID 1911755Notes

Reaction equation

HRID 1911755 reaction equation
[CH:1]1([CH2:4][N:5]([CH2:19][CH:20]2[CH2:22][CH2:21]2)[C:6]2[C:15]([CH:16]=O)=[CH:14][C:13]3[C:8](=[C:9]([CH3:18])[CH:10]=[CH:11][CH:12]=3)[N:7]=2)[CH2:3][CH2:2]1.[F:23][C:24]([F:38])([F:37])[C:25]1[CH:26]=[C:27]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[CH2:28][NH2:29].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[F:23][C:24]([F:37])([F:38])[C:25]1[CH:26]=[C:27]([CH:30]=[C:31]([C:33]([F:36])([F:34])[F:35])[CH:32]=1)[CH2:28][NH:29][CH2:16][C:15]1[C:6]([N:5]([CH2:19][CH:20]2[CH2:22][CH2:21]2)[CH2:4][CH:1]2[CH2:3][CH2:2]2)=[N:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:18]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5210993,5-Bis(trifluoromethyl)benzylamineHCID 5003444Sodium cyanoborohydrideHCID 574868222-(Bis(cyclopropylmethyl)amino)-8-methylquinoline-3-carbaldehyde

Product 1

HCID 574868233-((3,5-bis(trifluoromethyl)benzylamino)methyl)-N,N-bis(cyclopropylmethyl)-8-methylquinolin-2-amineYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(Bis(cyclopropylmethyl)amino)-8-methylquinoline-3-carbaldehyde (0.081 g, 0.39 mmol), 3,5-bis-trifluoromethylbenzylamine (0.096 g, 0.39 mmol) and acetic acid (0.047 g, 0.78 mmol) were put in a 25 mL RB flask. To this, 2 mL of methanol was added and stirred at RT for 15 min. Sodium cyanoborohydride (0.075 g, 0.77 mmol) was added portionwise and stirring was continued at RT for another 1 h. Methanol was removed from the reaction mixture under vacuum, water was added to this crude and was extracted with ethyl acetate (3×50 mL). The organic layer was washed with saturated NaHCO3 solution, brine and dried over sodium sulphate. The solvent was evaporated and the crude residue was purified by column chromatography over silica gel (100-200 mesh) eluting with 4% ethyl acetate in petroleum ether to give the title amine (0.142 g, yield: 99%).

Workup

  1. stirringstirring
  2. waitwas continued at RT for another 1 h
  3. customMethanol was removed from the reaction mixture under vacuum, water
  4. additionwas added to this crude
  5. extractionwas extracted with ethyl acetate (3×50 mL)
  6. washThe organic layer was washed with saturated NaHCO3 solution, brine
  7. dry with materialdried over sodium sulphate
  8. customThe solvent was evaporated
  9. customthe crude residue was purified by column chromatography over silica gel (100-200 mesh)
  10. washeluting with 4% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-4f9d2306faf24743a2e5e544bd799407
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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