2-Bromothiazole → 3-[4-(1,3-Thiazol-2-yl)piperazin-1-yl]propane-1,2-diol

HRID 231778Notes

Reaction equation

HRID 231778 reaction equation
[OH:1][CH:2]([CH2:10][OH:11])[CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.Br[C:13]1[S:14][CH:15]=[CH:16][N:17]=1>O1CCOCC1>[S:14]1[CH:15]=[CH:16][N:17]=[C:13]1[N:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH:2]([OH:1])[CH2:10][OH:11])[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 764302-BromothiazoleHCID 1110023-(Piperazin-1-yl)propane-1,2-diol

Product 1

HCID 200319943-[4-(1,3-Thiazol-2-yl)piperazin-1-yl]propane-1,2-diol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Grams 6.4 of 1-(2,3-dihydroxypropyl)piperazine and 3.3 g of 2-bromo-1,3-thiazole in 50 ml dioxane were refluxed for 24 hours. The reaction mixture was evaporated to dryness and the so obtained residue was purified on column eluting with chloroform:methanol (9:1). Grams 1.5 of 3-[4-(1,3-thiazol-2-yl)piperazin-1-yl] propane-1,2-diol which, by recrystallization from acetone, melted at 138°-139° C., were obtained.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe so obtained residue was purified on column
  3. washeluting with chloroform:methanol (9:1)
  4. customGrams 1.5 of 3-[4-(1,3-thiazol-2-yl)piperazin-1-yl] propane-1,2-diol which, by recrystallization from acetone, melted at 138°-139° C.
  5. customwere obtained

Sources & evidence

ORD record
ord-7f156dc1f729495b90bdff0555569ec5
Source dataset
uspto-grants-1989_07
Patent number
US04849422

Reaction notes

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