Potassium Carbonate → HCID 20482420, compound

HRID 648210Notes

Reaction equation

HRID 648210 reaction equation
Cl.Cl[CH2:3][C:4]1[N:5]=[CH:6][S:7][CH:8]=1.[CH:9]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:9]([N:22]1[CH2:27][CH2:26][N:25]([CH2:3][C:4]2[N:5]=[CH:6][S:7][CH:8]=2)[CH2:24][CH2:23]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70048BenzhydrylpiperazineHCID 27632894-(Chloromethyl)-1,3-thiazole hydrochloride

Product 1

HCID 20482420HCID 20482420, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 4-chloromethylthiazole monohydrochloride (1.7 g), 1-benzhydrylpiperazine (3.21 g) and potassium carbonate (5.3 g) in N,N-dimethylformamide (40 ml) was stirred at 65° C. for 2 hours. After concentration of the reaction mixture, the concentrate was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and then evaporated to dryness to give a residue, which was chromatographed on silica gel (120 g) using a mixture of chloroform and methanol (50:1 by volume) as an eluent. The eluates containing the desired compound were collected and evaporated to dryness under reduced pressure to give crystals, which were recrystallized from chloroform to obtain white crystals (1.2 g) of 4-(4-benzhydrylpiperazin-1-ylmethyl)thiazole, mp 114°-116° C.

Workup

  1. extractionAfter concentration of the reaction mixture, the concentrate was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated to dryness
  5. customto give a residue, which
  6. customwas chromatographed on silica gel (120 g)
  7. additiona mixture of chloroform and methanol (50:1 by volume) as an eluent
  8. additionThe eluates containing the desired compound
  9. customwere collected
  10. customevaporated to dryness under reduced pressure
  11. customto give crystals, which
  12. customwere recrystallized from chloroform

Sources & evidence

ORD record
ord-092b8bb227db4e659902748b99c5ede3
Source dataset
uspto-grants-1983_10
Patent number
US04411900

Reaction notes

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