1-{3-[(Quinolin-2-yl)methoxy]phenyl}hexan-1-ol → HCID 14349136, compound

HRID 414843Notes

Reaction equation

HRID 414843 reaction equation
[H-].[Na+].[OH:3][CH:4]([C:10]1[CH:11]=[C:12]([CH:25]=[CH:26][CH:27]=1)[O:13][CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[CH3:28]I>C(OCC)C>[CH3:28][O:3][CH:4]([C:10]1[CH:11]=[C:12]([CH:25]=[CH:26][CH:27]=1)[O:13][CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 50591-{3-[(Quinolin-2-yl)methoxy]phenyl}hexan-1-olHCID 6328Methyl iodideHCID 24758Sodium hydride

Product 1

HCID 14349136HCID 14349136, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of sodium hydride (0.5 g) in ethyl ether at 0° C. is added 2-[3-(1-hydroxyhexyl)phenoxymethyl]quinoline (1.8 g) in ether. The mixture is allowed to warm to room temperature. Methyl iodide (0.6 ml) is added and the reaction is stirred at room temperature for three days. The reaction mixture is quenched with saturated aqueous ammonium chloride and extracted with ethyl ether. The organic extract is washed with water, dried (MgSO4) and concentrated to an oil, which is purified by HPLC on silica gel using a 1:9 ratio of ethyl acetate/hexane as an eluent.

Workup

  1. customThe reaction mixture is quenched with saturated aqueous ammonium chloride
  2. extractionextracted with ethyl ether
  3. extractionThe organic extract
  4. washis washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated to an oil, which
  7. customis purified by HPLC on silica gel using a 1:9 ratio of ethyl acetate/hexane as an eluent

Sources & evidence

ORD record
ord-69016eb1462448a69dae68a1e73cf313
Source dataset
uspto-grants-1988_12
Patent number
US04794188

Reaction notes

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