Sodium Hydroxide → HCID 19911787, compound

HRID 1921665Notes

Reaction equation

HRID 1921665 reaction equation
C([O:3][C:4](=[O:15])[CH2:5][CH2:6][CH2:7][NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)C.[OH-].[Na+]>C1COCC1>[CH:9]1([NH:8][CH2:7][CH2:6][CH2:5][C:4]([OH:15])=[O:3])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 60683668HCID 60683668, compound

Product 1

HCID 19911787HCID 19911787, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7 g of 4-bromobutyric acid ethyl ester and 20 g of cyclohexylamine were added to 50 mL of ethanol, and the mixture was stirred at a room temperature for one week. The stirred 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 8.2 g of N-cyclohexyl-gamma-aminobutyric acid ethyl ester. The obtained N-cyclohexyl-gamma-aminobutyric acid ethyl ester was added to sodium hydroxide solution (1.68 g of sodium hydroxide/100 mL of purified water), and THF was added thereto till 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 4.1 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-843bfa919cf046ef9ba55579018e2fdc
Source dataset
uspto-grants-2012_05
Patent number
US08173705B2

Reaction notes

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