Benzyl Bromide → 94914-32-6

HRID 715118Notes

Reaction equation

HRID 715118 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:10]([N:2]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27563834-Aminobutyric acid methyl ester hydrochloride

Product 1

HCID 7887746894914-32-6Yield 91.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Heat a solution of methyl 4-aminobutanoate hydrochloride (11 g, 71.9 mmol), benzylbromide (25.2 g, 147.3 mmol) and K2CO3 (21.8 g, 158.2 mmol) in MeCN (200 mL) at 40° C. overnight. Concentrate the mixture to dryness, pour the residue into water, extract with EtOAc (3×), wash the combined organics with brine, dry over Na2SO4, concentrate and purify via silica gel chromatography to give the title compound (19.5 g, 91%). 1H NMR (400 MHz, DMSO-d6): δ 7.33-7.18 (m, 10H), 3.57 (s, 3H), 3.52 (s, 4H), 2.43-2.28 (m, 4H), 1.83-1.76 (m, 2H).

Workup

  1. concentrationConcentrate the mixture to dryness
  2. additionpour the residue into water
  3. extractionextract with EtOAc (3×)
  4. washwash the combined organics with brine
  5. dry with materialdry over Na2SO4
  6. concentrationconcentrate
  7. custompurify via silica gel chromatography

Sources & evidence

ORD record
ord-95f47a493c1a4f7ca2203b9c83015046
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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