Sodium Carbonate → HCID 67145119, compound

HRID 1887148Notes

Reaction equation

HRID 1887148 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[N:14][CH:13]=[CH:12][N:11]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[Br:16]N1C(=O)CCC1=O.C([O-])([O-])=O.[Na+].[Na+]>ClCCl>[Br:16][CH:5]1[CH2:6][N:7]([C:10]2[CH:15]=[N:14][CH:13]=[CH:12][N:11]=2)[CH2:8][CH2:9][N:4]1[CH:1]([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 67184N-bromobutanimide2×HCID 206138392-[4-(Propan-2-yl)piperazin-1-yl]pyrazine

Product 1

HCID 67145119HCID 67145119, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Isopropyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (1.0 g, 4.8 mmol) was dissolved in dichloromethane (30 mL) and the solution was placed on an ice-bath and brominated according to literature (Tetrahedron 44, 10, 1988, 2977-2984) in very bad yield. N-Bromosuccinimide (3.45 g, 19.4 mmol) was added slowly at 0° C. and then left overnight at rt. No reaction was observed. An additional 3.45 g of N-bromosuccinimide was added during 8 h, and then the reaction mixture was left at rt for 2 days. Aqueous concentrated Na2CO3 was added and the mixture was extracted with dichloromethane (3×75 mL). The combined organic extracts were dried (MgSO4), filtered and evaporated. The oily residue was purified on a silica gel column with dichloromethane/MeOH (9:1) as eluent. Yield: 196 mg (28%) of 5-bromo-4-isopropyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl as an oil.

Workup

  1. customthe solution was placed on an ice-bath
  2. waitthe reaction mixture was left at rt for 2 days
  3. extractionthe mixture was extracted with dichloromethane (3×75 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe oily residue was purified on a silica gel column with dichloromethane/MeOH (9:1) as eluent

Sources & evidence

ORD record
ord-6cd2b2cc1c354cf2b6b984f921062d58
Source dataset
uspto-grants-2013_08
Patent number
US08501739B2

Reaction notes

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