Sodium hydride → Ethyl N-(5-phenylpentyl)-beta-alaninate

HRID 1485118Notes

Reaction equation

HRID 1485118 reaction equation
[CH2:1](Cl)[CH3:2].[NH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[H-].[Na+].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O.C(OCC)(=O)C>[C:18]1([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][NH:4][CH2:5][CH2:6][C:7]([O:9][CH2:1][CH3:2])=[O:8])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 285561(5-Bromopentyl)benzeneHCID 131736734HCID 131736734, compound

Product 1

HCID 118113289Ethyl N-(5-phenylpentyl)-beta-alaninate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of β-alanine ethyl hydrochloride (2.00 g) in N,N-dimethylformamide (65.0 mL), sodium hydride (60% dispersion in mineral oil, 1.15 g) was added and the mixture was stirred at room temperature for an hour. After adding (5-bromopentyl)benzene (2.52 mL), the mixture was stirred at 80° C. for 4 hours. After being cooled to room temperature, the reaction mixture was diluted with ethyl acetate and washed with saturated brine. The organic layer was separated off and dried over anhydrous magnesium sulfate; after removing the desiccant by filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0-85:15) to give the titled compound as a pale yellow oil (480 mg).

Workup

  1. stirringthe mixture was stirred at 80° C. for 4 hours
  2. temperatureAfter being cooled to room temperature
  3. washwashed with saturated brine
  4. customThe organic layer was separated off
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customafter removing the
  7. filtrationdesiccant by filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0-85:15)

Sources & evidence

ORD record
ord-5726010410a04f0a92b5dd881db6b806
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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