Boron tribromide → 1-[4-(2-Fluorophenyl)-1,3-thiazol-2-yl]piperazine

HRID 2191545Notes

Reaction equation

HRID 2191545 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([N:13]2[CH2:18][CH2:17][N:16](C(OCC3C=CC=CC=3)=O)[CH2:15][CH2:14]2)[S:11][CH:12]=1.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([N:13]2[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]2)[S:11][CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 15984569Benzyl 4-(4-(2-fluorophenyl)thiazol-2-yl)piperazine-1-carboxylate

Product 1

HCID 581827331-[4-(2-Fluorophenyl)-1,3-thiazol-2-yl]piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-50 °C

Procedure

To a solution of benzyl 4-(4-(2-fluorophenyl)thiazol-2-yl)piperazine-1-carboxylate (0.85 g, 2.1 mmol) in CH2Cl2 (2 mL) cooled to −50° C. was added boron tribromide (1 M in CH2Cl2, 8.6 mL, 8.6 mmol). The reaction was stirred at −50° C. for 20 min and then carefully quenched with saturated aqueous NaHCO3. The mixture was extracted with CH2Cl2, and the combined extracts were washed with water, dried over Na2SO4, and concentrated under reduced pressure to yield 1-(4-(2-fluorophenyl)thiazol-2-yl)piperazine. LC/MS: m/z 264.1 (M+H)+ at 2.04 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customcarefully quenched with saturated aqueous NaHCO3
  2. extractionThe mixture was extracted with CH2Cl2
  3. washthe combined extracts were washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e2e821293caf4d1dabf025cf73ee5904
Source dataset
uspto-grants-2012_12
Patent number
US08329702B2

Reaction notes

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