Hydrochloric Acid → HCID 15817079, compound

HRID 2185825Notes

Reaction equation

HRID 2185825 reaction equation
[SH:1][C:2]1[N:6]([CH3:7])[CH:5]=[N:4][N:3]=1.Cl[CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[CH2:14][CH2:13]1.C(N(CC)CC)C.Cl>CN(C=O)C>[CH3:7][N:6]1[CH:5]=[N:4][N:3]=[C:2]1[S:1][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:25])[F:26])[CH:19]=2)[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 3060362Piperazine, 1-(3-chloropropyl)-4-(3-(trifluoromethyl)phenyl)-HCID 178481306HCID 178481306, compound

Product 1

HCID 15817079HCID 15817079, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.15 g (10 mmol) of 3-mercapto-4-methyl-4H-1,2,4-triazole, 3.1 g (10.1 mmol) of 1-(3-chloropropyl)-4-(3-trifluoromethylphenyl)piperazine and 1.5 g (15 mmol) of triethylamine in 5 ml of DMF were stirred at 100° C. for 1 hour. The mixture was then poured into 5% strength hydrochloric acid and extracted with ethyl acetate. The aqueous phase was made alkaline with sodium hydroxide solution and then extracted again with ethyl acetate, and the organic phase was dried over MgSO4 and concentrated. The residue was purified by chromatography (mobile phase: CH2Cl2/CH3OH=95/5). 2.1 g of product were obtained as a yellowish oil (=55% yield).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionextracted again with ethyl acetate
  3. dry with materialthe organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography (mobile phase: CH2Cl2/CH3OH=95/5)

Sources & evidence

ORD record
ord-6731e81df8ea4c7ea527d1c2456801a5
Source dataset
uspto-grants-2002_06
Patent number
US06403593B1

Reaction notes

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