Sodium Carbonate → [(6-Chloro(3-pyridyl))methyl](2-chloroethyl)[(4-methoxyphenyl)methyl]amine

HRID 549219Notes

Reaction equation

HRID 549219 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH:19](O)[CH3:20])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:24])=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:19][CH2:20][Cl:24])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 86624864[(6-Chloro(3-pyridyl)methyl][(4-methoxyphenyl)methyl]amino}ethan-1-ol

Product 1

HCID 86624865[(6-Chloro(3-pyridyl))methyl](2-chloroethyl)[(4-methoxyphenyl)methyl]amine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 6.8 grams (0.022 mole) of 2-{[(6-chloro(3-pyridyl)methyl][(4-methoxyphenyl)methyl]amino}ethan-1-ol in 200 mL of chloroform was stirred and a solution of 2.9 grams (0.024 mole) of thionyl chloride in 50 mL of chloroform was added dropwise. Upon completion of addition, the reaction mixture was stirred at ambient temperature during one hour, and then it was warmed to reflux where it stirred for 2.5 hours. After this time the reaction mixture was cooled to room temperature and was slowly poured into a solution of 100 mL of aqueous 5% sodium carbonate. The organic layer was separated and dried with sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel. Elution was accomplished using 2% diethyl ether in methylene chloride as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 6.4 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. temperatureit was warmed
  3. temperatureto reflux where it
  4. stirringstirred for 2.5 hours
  5. temperatureAfter this time the reaction mixture was cooled to room temperature
  6. customThe organic layer was separated
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure to a residue
  10. customThe residue was purified with column chromatography on silica gel
  11. washElution
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e8b070c6a3904b56b6235efefda9d019
Source dataset
uspto-grants-2011_05
Patent number
US07943642B2

Reaction notes

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