Dimethylamine → HCID 68544632, compound

HRID 1446744Notes

Reaction equation

HRID 1446744 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8]Br)=[N:6][CH:7]=1.[CH3:10][NH:11][CH3:12]>C1COCC1.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:11]([CH3:12])[CH3:10])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 234380625-Bromo-2-(bromomethyl)pyridine

Product 1

HCID 68544632HCID 68544632, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Place 5-bromo-2-bromomethyl-pyridine (1.7 g, 6.7 mmol, 1 eq) (Bioorg. Med. Chem. Lett. 1994, 4(1), 99) in a 250 mL round bottom short neck flask, dissolve in 100 mL of THF, cool to 0° C. and treat with a 2 M N,N-dimethylamine solution in THF (9 mL, 18 mmol, 2.7 eq). After 2 hours, concentrate the reaction, dilute with 50 mL of CH2Cl2, and wash with 20 mL of water. Dry the organics and concentrate to give 0.90 g (64%) of the title compound as a brown oil. MS (ES), m/z 217 (M+1).

Workup

  1. concentrationconcentrate
  2. customthe reaction
  3. washwash with 20 mL of water
  4. customDry the organics and
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-e484e11b94cc40198f5192d1930328a9
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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