Benzyl Bromide → N-Boc-N-benzyl-3-chloropropylamine

HRID 321948Notes

Reaction equation

HRID 321948 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][CH2:11][Cl:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1.CCOCC.O>[C:1]([N:8]([CH2:9][CH2:10][CH2:11][Cl:12])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 10932310N-Boc-3-Chloropropylamine

Product 1

HCID 11098062N-Boc-N-benzyl-3-chloropropylamineYield 13.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-Boc-3-chloropropylamine (10.0 g, 51.8 mmol) in THF was added sodium hydride (1.87 g, 78 mmol). After 20 min, benzyl bromide (9.24 mL, 78 mmol) was added and the reaction mixture was heated at reflux for 16 h. After cooling, the reaction mixture was diluted with Et2O (150 mL) and H2O (50 mL), the layers were separated and the aqueous layer was extracted twice with Et2O. The combined organic phases were washed with H2O and brine, dried (MgSO4), filtered and concentrated. The resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane) to give N-Boc-N-benzyl-3-chloropropylamine (1.97 g, 13% yield) as a pale yellow oil.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. temperatureAfter cooling
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted twice with Et2O
  6. washThe combined organic phases were washed with H2O and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane)

Sources & evidence

ORD record
ord-256e366c627e4932a36fa4f2e340f0d0
Source dataset
uspto-grants-2001_04
Patent number
US06211170B1

Reaction notes

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