(3-Bromopropyl)benzene → HCID 178421606, compound

HRID 353119Notes

Reaction equation

HRID 353119 reaction equation
[CH3:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[N:18]=[CH:17][NH:16][N:15]=3)[CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(=O)([O-])O.[Na+].Br[CH2:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C)C=O>[NH3:5].[CH3:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[N:18]=[CH:17][NH:16][N:15]=3)[CH:9]=2)[CH2:3][CH2:4][N:5]([CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 12503(3-Bromopropyl)benzeneHCID 516892Sodium BicarbonateHCID 178421604HCID 178421604, compound

Product 2

HCID 222AmmoniaHCID 178421606HCID 178421606, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-methyl-4-(3-(1H-1,2,4-triazol-3-yl)phenyl)piperidine (Preparation 45, 65 mg, 0.27 mmol) in N,N-dimethylformamide (2 mL) was added sodium hydrogencarbonate (34 mg, 0.40 mmol) and 1-bromo-3-phenylpropane (41 μL, 0.27 mmol). The resultant mixture was heated at 50° C. for 2 h and then allowed to cool. The mixture was partitioned between water (5 mL) and dichloromethane (20 mL). The layers were separated, and the aqueous layer was extracted with dichloromethane (20 mL). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by column chromatography on silica gel (5 g) eluting with MeOH:CH2Cl2:0.88 ammonia (10:90:1) to give the title compound as a clear oil (13 mg, 13%).

Workup

  1. temperatureto cool
  2. customThe mixture was partitioned between water (5 mL) and dichloromethane (20 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane (20 mL)
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customthe residue was purified by column chromatography on silica gel (5 g)
  9. washeluting with MeOH

Sources & evidence

ORD record
ord-c89b3e9ccc7243a6b7e7de31f2df89a2
Source dataset
uspto-grants-2004_06
Patent number
US06750231B2

Reaction notes

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