Water → 3-(Cyclohexylmethoxy)pyridin-2-amine

HRID 2401625Notes

Reaction equation

HRID 2401625 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][N:5]=1.[CH:11]1([CH2:17]Br)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.O>CO>[CH:11]1([CH2:17][O:10][C:9]2[C:4]([NH2:3])=[N:5][CH:6]=[CH:7][CH:8]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 281142-Amino-3-HydroxypyridineHCID 137636Cyclohexane, (bromomethyl)-

Product 1

HCID 138258903-(Cyclohexylmethoxy)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At RT, 96 g of aqueous sodium hydroxide solution (45%; 1081 mmol, 1 equivalent) were initially charged in 1170 ml of methanol, 119 g of 2-amino-3-hydroxypyridine (1080 mmol, 1 equivalent) were added and the mixture was stirred at RT for 10 min. The reaction mixture was concentrated under reduced pressure, the residue was taken up in 2900 ml of DMSO and 101 g of cyclohexylmethyl bromide (1135 mmol, 1.05 equivalents) were added. After 16 h at RT, the reaction mixture was stirred into 61 of water, the aqueous solution was extracted twice with in each case 2 l of ethyl acetate, the combined organic phases were washed with in each case 1 l of saturated aqueous sodium bicarbonate solution and water, dried, filtered and concentrated. The residue was triturated with 500 ml of n-pentane, filtered off and dried under reduced pressure. This gave 130 g (58.3% of theory) of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. waitAfter 16 h at RT
  3. extractionthe aqueous solution was extracted twice with in each case 2 l of ethyl acetate
  4. washthe combined organic phases were washed with in each case 1 l of saturated aqueous sodium bicarbonate solution and water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was triturated with 500 ml of n-pentane
  9. filtrationfiltered off
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-8d1bd4665ca94900a5fad42dd6100c88
Source dataset
uspto-grants-2014_08
Patent number
US08796305B2

Reaction notes

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