1-Bromohexane → HCID 178444682, compound

HRID 353118Notes

Reaction equation

HRID 353118 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][CH2:28][CH2:29][CH3:30]>CN(C)C=O>[NH3:5].[CH2:25]([N:5]1[CH2:4][CH2:3][C:2]([CH3:1])([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]1)[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 3

HCID 81011-BromohexaneHCID 516892Sodium BicarbonateHCID 178421604HCID 178421604, compound

Product 2

HCID 222AmmoniaHCID 178444682HCID 178444682, compoundYield 18.6%

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, 55 mg, 0.23 mmol) in N,N-dimethylformamide (2 mL) was added sodium hydrogencarbonate (28 mg, 0.34 mmol) and bromohexane (32 μL, 0.23 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 silica (5 g) column chromatography eluting with methanol:dichloromethane:0.88 ammonia (10:90:1) to give the title compound as a clear oil (7 mg, 9%).

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 silica (5 g) column chromatography
  9. washeluting with methanol

Sources & evidence

ORD record
ord-d9dc504467124fc1881a73347d452b45
Source dataset
uspto-grants-2004_06
Patent number
US06750231B2

Reaction notes

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