Water → {2-[n-(Cyclohexylmethyl)-n-ethylamino]-7-fluoroquinolin-3-yl}methanol

HRID 1518057Notes

Reaction equation

HRID 1518057 reaction equation
[CH:1]1([CH2:7][N:8]([C:11]2[C:20]([CH:21]=[O:22])=[CH:19][C:18]3[C:13](=[CH:14][C:15]([F:23])=[CH:16][CH:17]=3)[N:12]=2)[CH2:9][CH3:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].[Cl-].[NH4+].O>C(O)C>[CH:1]1([CH2:7][N:8]([C:11]2[C:20]([CH2:21][OH:22])=[CH:19][C:18]3[C:13](=[CH:14][C:15]([F:23])=[CH:16][CH:17]=3)[N:12]=2)[CH2:9][CH3:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 57861258HCID 57861258, compound

Product 1

HCID 57861244{2-[n-(Cyclohexylmethyl)-n-ethylamino]-7-fluoroquinolin-3-yl}methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2-[N-(cyclohexylmethyl)-N-ethylamino]-7-fluoroquinoline-3-carbaldehyde (230 mg, 0.73 mmol) in ethanol (2 mL) is added sodium borohydride (30 mg, 0.79 mmol) and the mixture is stirred for 2 hours. After addition of sat. ammonium chloride and water, the mixture is extracted with ethyl acetate. The combined organic layer is washed with brine, dried over magnesium sulfate, filtered and concentrated to give [N-(cyclopentylmethyl)-N-ethylamino]quinolin-3-yl}methanol, which is used without further purification.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe combined organic layer is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give [N-(cyclopentylmethyl)-N-ethylamino]quinolin-3-yl}methanol, which
  7. customis used without further purification

Sources & evidence

ORD record
ord-0bc0355c436a4dc7b923ef691d4060af
Source dataset
uspto-grants-2012_07
Patent number
US08232403B2

Reaction notes

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