Sodium Hydroxide → 4-(Cyclohexylmethylamino)butanoic acid

HRID 1921667Notes

Reaction equation

HRID 1921667 reaction equation
C([O:3][C:4](=[O:16])[CH2:5][CH2:6][CH2:7][N:8]([CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[CH3:9])C.[OH-].[Na+]>C1COCC1>[CH:10]1([N:8]([CH3:9])[CH2:7][CH2:6][CH2:5][C:4]([OH:16])=[O:3])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67493517N-cyclohexyl-N-methyl-gamma-aminobutyric acid ethyl ester

Product 1

HCID 209853894-(Cyclohexylmethylamino)butanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10 g of 4-bromobutyric acid ethyl ester and 15 g of N-cyclohexyl-N-methylamine were added to 40 mL of ethanol, and the mixture was heated to reflux for 2 hours. After air-cooling, the mixture was concentrated under reduced pressure and extracted with 200 mL of ethyl acetate. The extracted material was washed with purified water, dried with magnesium sulfate, and then concentrated. The obtained residue was distilled under reduced pressure to give 10.5 g of N-cyclohexyl-N-methyl-gamma-aminobutyric acid ethyl ester. The obtained N-cyclohexyl-N-methyl-gamma-aminobutyric acid ethyl ester was added to a sodium hydroxide solution (2.4 g of sodium hydroxide/100 mL of purified water), and THF was added thereto until the mixture became homogeneous. After stirring at room temperature for 3 hours, the mixture was neutralized with DOWEX50W [H+ form] and concentrated under reduced pressure. The obtained residue was recrystallized to give 5.2 g of the desired product.

Workup

  1. additionwas added
  2. concentrationconcentrated under reduced pressure
  3. customThe obtained residue was recrystallized

Sources & evidence

ORD record
ord-ccf591cba32948f98850ca814757a2fc
Source dataset
uspto-grants-2012_05
Patent number
US08173705B2

Reaction notes

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