Hydrochloric Acid → HCID 69003272, compound

HRID 1436095Notes

Reaction equation

HRID 1436095 reaction equation
O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:21]([CH:24]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][N:27]=1)[CH3:25])=[N+]=[N-].Cl>O1CCCC1.ClCCl>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([CH:24]([NH2:21])[CH3:25])=[N:27][CH:28]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11776TriphenylphosphineHCID 86612606HCID 86612606, compound

Product 1

HCID 69003272HCID 69003272, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Water (3 mL) and triphenylphosphine (702 mg) were added to a solution of 2-(1-azidoethyl)-5-chloropyridine (333 mg) in tetrahydrofuran (10 mL), and the reaction solution was stirred at 60° C. for two hours. The reaction solution was returned to room temperature. Dichloromethane and 5 N hydrochloric acid were added to the reaction solution, and the aqueous layer was separated. The aqueous layer was made basic (pH 14) with a 5 N sodium hydroxide solution. Then, dichloromethane was added to the reaction solution, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain 260 mg of the title compound.

Workup

  1. customwas returned to room temperature
  2. customthe aqueous layer was separated
  3. additionThen, dichloromethane was added to the reaction solution
  4. customthe organic layer was separated
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-bf5be42d5539413faaf02a75797ef00d
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

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