Pentanal → 2-(4-n-Pentylaminophenoxymethyl)quinoline

HRID 727807Notes

Reaction equation

HRID 727807 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.C([BH3-])#N.[Na+].[CH:24](=O)[CH2:25][CH2:26][CH2:27][CH3:28]>CO>[CH2:24]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:18][CH:19]=1)[CH2:25][CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 8063PentanalHCID 27475694-(Quinolin-2-ylmethoxy)anilineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 198018952-(4-n-Pentylaminophenoxymethyl)quinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

12.5 g (0.05 mol) of the compound from Example 1 were dissolved in methanol. 2.0 g (0.03 mol) of sodium cyanoborohydride were then added in portions. 5.3 ml (0.05 mol) of pentanal were cautiously added dropwise to the solution. After stirring for 48 h at room temperature, the solution was concentrated in vacuo, the residue was dissolved in methylene chloride and the solution was washed with 2N hydrochloric acid. The organic phase was separated off, dried and concentrated in vacuo, and the residue was put through a 1000 cm3 silica gel 60 column. The system methylene chloride/ethyl acetate 7:3 was employed as the eluent.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washthe solution was washed with 2N hydrochloric acid
  4. customThe organic phase was separated off
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4e67c9e6246d42b9b21e5376d16e3cae
Source dataset
uspto-grants-1991_09
Patent number
US05045547

Reaction notes

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