Water → HCID 18357143, compound

HRID 427470Notes

Reaction equation

HRID 427470 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:3][CH:2]=1.Br[C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][N:15]=1.O>CO>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([N:10]2[CH2:9][CH2:8][N:7]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[CH2:12][CH2:11]2)=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 693532,5-DibromopyridineHCID 705171-(4-Pyridyl)piperazine

Product 1

HCID 18357143HCID 18357143, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 1-(4-pyridyl)piperazine (3.26 g, 20 mmol) and 2,5-dibromopyridine (2.36 g) was heated gradually on an oil bath up to 200° C. At approximately 150° C. a clear, slightly coloured melt was obtained and at approximately 180° C. a vigorous reaction set in which caused the melt to darken markedly. The now-dark melt was heated at 200° C. for 10 minutes then allowed to cool to room temperature. The solid reaction mixture was dissolved in methanol (100 mL) and poured into water (100-150 mL). The resultant precipitate was collected, washed with water, dried, then recrystallised from hot aqueous methanol to give the product (1.6 g, 25% yield) as a buff-coloured solid: m.p. 176-180° C.; NMR (DMSO-d6), 3.32 (4H, m), 3.50 (4H, m), 6.72 (2H, m), 6.75 (1H, d), 7.59 (1H, dd), 8.05 (3H, m); Found: MH+, 319/321; C14H15BrN4 requires MH+, 319/321.

Workup

  1. customAt approximately 150° C. a clear, slightly coloured melt was obtained and at approximately 180° C. a vigorous reaction set in which
  2. temperatureThe now-dark melt was heated at 200° C. for 10 minutes
  3. temperatureto cool to room temperature
  4. customThe solid reaction mixture
  5. customThe resultant precipitate was collected
  6. washwashed with water
  7. customdried
  8. customrecrystallised from hot aqueous methanol

Sources & evidence

ORD record
ord-4aaf7ab605b44820a71df0f175a1085a
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Reaction notes

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