Water → HCID 57861234, compound

HRID 1518054Notes

Reaction equation

HRID 1518054 reaction equation
[CH:1]1([CH2:6][N:7]([C:10]2[C:19]([CH:20]=[O:21])=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH2:8][CH3:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].[Cl-].[NH4+].O>C(O)C>[CH:1]1([CH2:6][N:7]([C:10]2[C:19]([CH2:20][OH:21])=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH2:8][CH3:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 574444392-[(Cyclopentylmethyl)(ethyl)amino]quinoline-3-carbaldehyde

Product 1

HCID 57861234HCID 57861234, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-[N-(cyclopentylmethyl)-N-ethylamino]quinoline-3-carbaldehyde (25 mg, 0.088 mmol) in ethanol (1 mL) is added sodium borohydride (5 mg, 0.13 mmol) and the mixture is stirred for 1 hour. 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 {2-[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

Sources & evidence

ORD record
ord-08e86a5e153048bf92788db860f688c1
Source dataset
uspto-grants-2012_07
Patent number
US08232403B2

Reaction notes

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