1-Bromopentane → HCID 178446093, compound

HRID 353112Notes

Reaction equation

HRID 353112 reaction equation
[CH3:1][CH:2]1[C:7]([CH3:19])([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[N:15]=[N:16][NH:17][CH:18]=3)[CH:9]=2)[CH2:6][CH2:5][NH:4][CH2:3]1.Br[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:1][CH:2]1[C:7]([CH3:19])([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[N:15]=[N:16][NH:17][CH:18]=3)[CH:9]=2)[CH2:6][CH2:5][N:4]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:3]1

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 516892Sodium Bicarbonate2×HCID 178430465HCID 178430465, compound

Product 1

HCID 178446093HCID 178446093, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,4-dimethyl-4-(3-(1H-1,2,3-triazol-4-yl)phenyl)piperidine (Preparation 44, 45 mg, 0.18 mmol) in N,N-dimethylformamide (5 mL) was added commercially available bromopentane (29 mg, 0.19 mmol) and sodium hydrogencarbonate (30 mg, 0.35 mmol). The resultant mixture was heated to 80° C. and stirred overnight. The reaction mixture was cooled, poured onto saturated aqueous sodium hydrogen-carbonate solution (100 mL) and extracted with ethyl acetate (3×20 mL). The combined extracts were dried over MgSO4, filtered and concentrated in vacuo to give an off-white gum. The crude product was purified by reverse phase high performance liquid chromatography (condition 1) to give the title compound as a clear oil (33 mg, 57.3%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combined extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give an off-white gum
  7. customThe crude product was purified by reverse phase high performance liquid chromatography (condition 1)

Sources & evidence

ORD record
ord-4c231d21962b461393bee9cc611d35f0
Source dataset
uspto-grants-2004_06
Patent number
US06750231B2

Reaction notes

Loading…