Trifluoroacetic acid → 6-Bromo-2-(piperidin-4-yloxy)-benzothiazole

HRID 1429521Notes

Reaction equation

HRID 1429521 reaction equation
[Br:1][C:2]1[CH:24]=[CH:23][C:5]2[N:6]=[C:7]([O:9][CH:10]3[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]3)[S:8][C:4]=2[CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[CH:24]=[CH:23][C:5]2[N:6]=[C:7]([O:9][CH:10]3[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]3)[S:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 674666144-(6-Bromo-benzothiazol-2-yloxy)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 674668246-Bromo-2-(piperidin-4-yloxy)-benzothiazoleYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 4-(6-bromobenzo[d]thiazol-2-yloxy)piperidine-1-carboxylate (257 mg, 0.622 mmol) in CH2Cl2 (5 mL) was added TFA (0.719 mL, 9.33 mmol). After 2 h, the reaction mixture was diluted with DCM and washed with 1N NaOH and then brine, dried over Na2SO4, filtered and then concentrated under reduced pressure to obtain Compound 1B as a light yellow solid (190 mg, 0.607 mmol, 98% yield). 1H NMR (500 MHz, chloroform-d) δ ppm 7.75 (1H, d, J=1.9 Hz), 7.48-7.52 (1H, m), 7.43-7.47 (1H, m), 5.21-5.29 (1H, m), 3.15 (2H, dt, J=12.9, 4.7 Hz), 2.80 (2H, ddd, J=12.7, 9.5, 3.2 Hz), 2.10-2.22 (2H, m), 1.71-1.84 (2H, m), 1.47 (1H, br. s.).

Workup

  1. washwashed with 1N NaOH
  2. dry with materialbrine, dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ca4bc4e351574c8da8ffad57a304b327
Source dataset
uspto-grants-2015_01
Patent number
US08940716B2

Reaction notes

Loading…