Trifluoroacetic acid → 2-(4-tert-Butyl-phenyl)-4-piperazin-1-yl-benzooxazole

HRID 491420Notes

Reaction equation

HRID 491420 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]3[N:20]=[C:21]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=4)[O:22][C:18]=3[CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:29]([C:26]1[CH:25]=[CH:24][C:23]([C:21]2[O:22][C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([N:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[C:19]=3[N:20]=2)=[CH:28][CH:27]=1)([CH3:32])([CH3:30])[CH3:31]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 576783004-[2-(4-tert-Butyl-phenyl)-benzooxazol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 576783102-(4-tert-Butyl-phenyl)-4-piperazin-1-yl-benzooxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[2-(4-tert-butyl-phenyl)-benzooxazol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (900 mg, 2.07 mmol) was stirred in a solution of concentrated trifluoroacetic acid (20 mL) and methylene chloride (20 mL) under N2 at room temperature for 5 h. The solvent was removed in vacuo and the oil was transferred to a separatory funnel with ethyl acetate (150 mL) and washed with 1M aqueous potassium carbonate solution (100 mL×2). The aqueous washings were combined and extracted with ethyl acetate (150 mL). The organic extracts were combined and washed with brine (100 mL), dried (Na2SO4), filtered and the filtrate concentrated to give a clear oil which was concentrated in vacuo with hexane several times to give a waxy material which was placed on a drying pistol overnight to afford the product as an amber colored wax (550 mg, 79%). Mass Spectrum (+ESI): 336 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe oil was transferred to a separatory funnel with ethyl acetate (150 mL)
  3. washwashed with 1M aqueous potassium carbonate solution (100 mL×2)
  4. extractionextracted with ethyl acetate (150 mL)
  5. washwashed with brine (100 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated
  9. customto give a clear oil which
  10. concentrationwas concentrated in vacuo with hexane several times
  11. customto give a waxy material which
  12. customwas placed on a drying pistol overnight
  13. customto afford the product as an amber colored wax (550 mg, 79%)

Sources & evidence

ORD record
ord-d021ccfce90343f2a2580e3a291ab466
Source dataset
uspto-grants-2009_05
Patent number
US07531542B2

Reaction notes

Loading…