1,4-Dioxane hydrochloride → HCID 59555849, compound

HRID 1725463Notes

Reaction equation

HRID 1725463 reaction equation
[Br:1][C:2]1[S:6][C:5](=[N:7][C:8]2[N:13]=[C:12]([CH2:14][N:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:28])[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:17][CH2:16]3)[CH:11]=[CH:10][CH:9]=2)[N:4](COC)[CH:3]=1.Cl.O1CCOCC1>C(Cl)(Cl)Cl>[Br:1][C:2]1[S:6][C:5]([NH:7][C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([CH2:14][N:15]3[CH2:16][CH2:17][N:18]([C:21](=[O:28])[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:19][CH2:20]3)[N:13]=2)=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 68679536HCID 68679536, compound

Product 1

HCID 59555849HCID 59555849, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

81 mg (0.161 mmol) of 1-(6-(5-bromo-3-methoxymethyl-3H-thiazol-2-ylideneamino)-pyridin-2-ylmethyl)4-benzoyl-piperazine was dissolved in 10 ml of chloroform, a hydrochloric acid-1,4-dioxane solution (4 M, 4 ml) was added thereto and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo, the residue was recrystallized from methanol-ether and filtered and the resulting white solid was dissolved in water (10 ml) and neutralized with sodium bicarbonate. The resulting precipitate was filtered to give 32 mg (0.070 mmol) of the title compound as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was recrystallized from methanol-ether
  3. filtrationfiltered
  4. dissolutionthe resulting white solid was dissolved in water (10 ml)
  5. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-b45a37ded76342efbdb9deca3556b616
Source dataset
uspto-grants-2009_02
Patent number
US07491720B2

Reaction notes

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