Acetone → HCID 59543454, compound

HRID 1798942Notes

Reaction equation

HRID 1798942 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.[CH3:14][C:15](=O)[CH3:16].Cl>C(O)(=O)C.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([CH:15]([CH3:16])[CH3:14])[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 57980628HCID 57980628, compound

Product 1

HCID 59543454HCID 59543454, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

5-Bromo-1′,2′,3′,4′,5′,6′-hexahydro-[2,4′]bipyridinyl (6.7 g, 18.9 mmol) was dissolved in 2% acetic acid in MeOH (40 ml). Propanone (8 mL, 113 mmol) and Na(CN)BH3 (3.6 g, 57 mmol) were added. The reaction mixture was stirred at RT over night. LC-MS showed only product. The reaction mixture was added 1N HCl filtered and evaporated in vacuo. The compound was dissolved in water pH was adjusted to PH=12 extracted with DCM (3×200 mL). The DCM phase was dried with Na2CO3 filtered and evaporation gave 4.4 g (82%) white crystals.

Workup

  1. filtrationfiltered
  2. customevaporated in vacuo
  3. dissolutionThe compound was dissolved in water
  4. extractionextracted with DCM (3×200 mL)
  5. dry with materialThe DCM phase was dried with Na2CO3
  6. filtrationfiltered
  7. customevaporation

Sources & evidence

ORD record
ord-6bb28149d2144a889ff0e6a2874cdb95
Source dataset
uspto-grants-2013_01
Patent number
US08344001B2

Reaction notes

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