2,4-Dimethoxybenzylamine → (7-Bromo-quinolin-2-ylmethyl)-(2,4-dimethoxy-benzyl)-amine

HRID 2176222Notes

Reaction equation

HRID 2176222 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=O)=[N:9]2)=[CH:4][CH:3]=1.[CH3:14][O:15][C:16]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:17]=1[CH2:18][NH2:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][NH:19][CH2:18][C:17]3[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:16]=3[O:15][CH3:14])=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5972502,4-DimethoxybenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 366880237-Bromo-2-quinolinecarboxaldehyde

Product 1

HCID 86706058(7-Bromo-quinolin-2-ylmethyl)-(2,4-dimethoxy-benzyl)-amineYield 98.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

7-Bromo-quinoline-2-carbaldehyde (354 mg, 1.50 mmol, prepared as described in EP 239746) was dissolved in 1,2-dichloroethane (15 mL) and 2,4-dimethoxybenzylamine (251 mg, 225 μL, 1.50 mmol) was added and the reaction mixture stirred for 5 minutes before sodium triacetoxyborohydride (477 mg, 2.25 mmol) was added. After 3.5 h stirring the reaction mixture was quenched with saturated sodium hydrogen carbonate solution and ethyl acetate was added. The organic layer was separated and washed with sodium hydrogen carbonate and the combined aqueous layers were extracted with ethyl acetate. The organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered and evaporated to give the crude, title compound as a yellow gum (571 mg) which was used without further purification. LCMS (m/z) 387.0, 389.0 [M+H], Tr=1.57 min.

Workup

  1. additionwas added
  2. customwas quenched with saturated sodium hydrogen carbonate solution and ethyl acetate
  3. additionwas added
  4. customThe organic layer was separated
  5. washwashed with sodium hydrogen carbonate
  6. extractionthe combined aqueous layers were extracted with ethyl acetate
  7. washThe organic extracts were washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-03424f6dcdc7400dadfbd1ff3c5df6f6
Source dataset
uspto-grants-2015_06
Patent number
US09062092B2

Reaction notes

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