Thionyl Chloride → (6-Chloro(3-pyridyl)methyl](2-chloroethyl)[(4-chlorophenyl)methyl]amine

HRID 549227Notes

Reaction equation

HRID 549227 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH:18](O)[CH3:19])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:23])=O>N1C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:18][CH2:19][Cl:23])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 86624869[(6-Chloro(3-pyridyl)methyl][(4-chlorophenyl)methyl]amino}ethan-1-ol

Product 1

HCID 86624870(6-Chloro(3-pyridyl)methyl](2-chloroethyl)[(4-chlorophenyl)methyl]amine

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6212ChloroformSolvent

Procedure

This compound was prepared in a manner analogous to that set forth in Step C of Example 1, using 6.0 grams (0.0193 mole) of 2-{[(6-chloro(3-pyridyl)methyl][(4-chlorophenyl)methyl]amino}ethan-1-ol, 2.4 grams (0.0203 mole) of thionyl chloride and four drops (catalyst) of pyridine in 75 mL of chloroform. The crude product was purified with column chromatography on silica gel. Elution was accomplished using 15% ethyl acetate in hexane then 30% ethyl acetate in hexane as eluants. The appropriate fractions were combined and concentrated under reduced pressure, yielding 5.7 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThis compound was prepared in a manner analogous to that set forth in Step C of Example 1
  2. customThe crude product was purified with column chromatography on silica gel
  3. washElution
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f1add152c4734c3dbba54b81ea63b0d5
Source dataset
uspto-grants-2011_05
Patent number
US07943642B2

Reaction notes

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