1,4-Dioxane hydrochloride → HCID 59555849, compound

HRID 1172406Notes

Reaction equation

HRID 1172406 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-c7ea08a3647d44bcb846fc6a2e35d48b
Source dataset
uspto-grants-2010_11
Patent number
US07834018B2

Reaction notes

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