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

HRID 2275756Notes

Reaction equation

HRID 2275756 reaction equation
[OH-].[Na+].O.[NH2:4][C:5]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][N:6]=1.[CH:12]1([CH2:18]Br)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>CO>[CH:12]1([CH2:18][O:11][C:10]2[C:5]([NH2:4])=[N:6][CH:7]=[CH:8][CH:9]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 962Water2×HCID 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 sodium hydroxide 45% strength in water (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 added slowly to 6 l of water and the aqueous solution was extracted twice with in each case 21 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 and dried under reduced pressure. This gave 130 g (58% 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 21 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
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-be093959ea8b46099be8a39c8ed20bf7
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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