Sodium Bicarbonate → HCID 178424991, compound

HRID 353111Notes

Reaction equation

HRID 353111 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][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[CH:24]=1.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][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[CH:24]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 516892Sodium Bicarbonate2×HCID 5706841-(2-Bromoethyl)-3-methylbenzeneHCID 178430465HCID 178430465, compound

Product 1

HCID 178424991HCID 178424991, compoundYield 12.9%

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, 80 mg, 0.31 mmol) in N,N-dimethyl-formamide (6 mL) was added 1-(2-bromoethyl)-3-methylbenzene (Preparation 46, 67 mg, 0.31 mmol) and sodium hydrogencarbonate (40 mg, 0.47 mmol). The resultant mixture was heated to 80° C. and stirred overnight. The reaction mixture was cooled, poured onto saturated aqueous sodium hydrogencarbonate 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 partially purified by column chromatography on a 5 g silica Waters Sep-Pak3 eluting with dichloromethane and then 5% methanol in dichloromethane. The pure fractions were collected to give the title compound as a clear oil (15 mg, 12.8%).

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 partially purified by column chromatography on a 5 g silica Waters Sep-Pak3
  8. washeluting with dichloromethane
  9. customThe pure fractions were collected

Sources & evidence

ORD record
ord-0fcbac1785e34b3a9f17d4cc1deb2bbb
Source dataset
uspto-grants-2004_06
Patent number
US06750231B2

Reaction notes

Loading…