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

HRID 1960013Notes

Reaction equation

HRID 1960013 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-5eec75b9b8044723b15daa36284ad340
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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