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

HRID 1624061Notes

Reaction equation

HRID 1624061 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 sodium hydroxide (45%; 1081 mmol, 1 equivalents) 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 6 l of water, and the aqueous solution was extracted twice, in each case with 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 stirred with 500 ml of 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, in each case with 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. stirringThe residue was stirred with 500 ml of pentane
  9. filtrationfiltered off
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-fa384b853c8b4fd2bdccc93a36f6f0d4
Source dataset
uspto-grants-2014_07
Patent number
US08778964B2

Reaction notes

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