Trifluoroacetic acid → 4-[4-(4,5-Dihydrooxazol-2-yl)phenyl]piperazine

HRID 650928Notes

Reaction equation

HRID 650928 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[O:21][CH2:22][CH2:23][N:24]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1.CO.C(N(CC)CC)C>[O:21]1[CH2:22][CH2:23][N:24]=[C:20]1[C:17]1[CH:18]=[CH:19][C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:15][CH:16]=1

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18504842n-Tert-butoxycarbonyl-4-[4-(4,5-dihydrooxazol-2-yl)phenyl]piperazine

Product 1

HCID 185048344-[4-(4,5-Dihydrooxazol-2-yl)phenyl]piperazine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

Compound 5A (826 mg; 2.49 mmol) in solution in toluene (20 ml) is treated, at room temperature, with trifluoroacetic acid (2.75 ml). After 1 h, the medium is evaporated to dryness and coevaporated 3 times with toluene. The product obtained is taken up in methanol (20 ml) and triethylamine (8 ml), stirred for 15 min at room temperature and finally evaporated to dryness. The solid obtained is purified by chromatography on a silica gel column eluted with a dichloro-methane/methanol/ammonium hydroxide mixture in the proportions 90/9/1 to give the intermediate 5B.

Workup

  1. customthe medium is evaporated to dryness
  2. customThe product obtained
  3. customfinally evaporated to dryness
  4. customThe solid obtained
  5. customis purified by chromatography on a silica gel column
  6. washeluted with a dichloro-methane/methanol/ammonium hydroxide mixture in the proportions 90/9/1

Sources & evidence

ORD record
ord-a21c3b9c151343858ede89557582c309
Source dataset
uspto-grants-2001_08
Patent number
US06277853B1

Reaction notes

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