1,4-Dibromobutane → Ammonia

HRID 1937043Notes

Reaction equation

HRID 1937043 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH2:15][CH:14]3[N:16]([CH3:17])[CH:10]([CH2:11][CH2:12][CH2:13]3)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][CH2:27][CH2:28]Br>C(O)C>[NH3:1].[N:1]1([C:2]2[CH:3]=[C:4]([C:8]3[CH2:9][CH:10]4[N:16]([CH3:17])[CH:14]([CH2:13][CH2:12][CH2:11]4)[CH:15]=3)[CH:5]=[CH:6][CH:7]=2)[CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

6

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 22463286HCID 22463286, compound

Product 2

HCID 222AmmoniaHCID 22463288HCID 22463288, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (±)-3-(3-aminophenyl)-9-methyl-9-azabicyclo[3.3.1]non-2-ene (0.50 g, 2.2 mmol), potassium carbonate (0.61 g, 4.4 mmol), 1.4-dibromobutane (0.52 g, 2.4 mmol) and ethanol (15 ml) was stirred at reflux overnight. The mixture was evaporated and water (25 ml) was added followed by extraction two times with ethyl acetate (25 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound as an oil. Yield 0.12 g, 19%.

Workup

  1. temperatureat reflux overnight
  2. customThe mixture was evaporated
  3. additionwater (25 ml) was added
  4. extractionfollowed by extraction two times with ethyl acetate (25 ml)

Sources & evidence

ORD record
ord-a342842b8b814c09b28375e54b9a5083
Source dataset
uspto-grants-2002_05
Patent number
US06392045B1

Reaction notes

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