Trifluoroacetic acid → 1-(2,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazine

HRID 1272295Notes

Reaction equation

HRID 1272295 reaction equation
FC(F)(F)C(O)=O.O[C:9]1([C:37]2[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=2)[C:13]2[C:14]([CH3:34])=[C:15]([N:20]3[CH2:25][CH2:24][N:23]([C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=4)[CH2:22][CH2:21]3)[C:16]([CH3:19])=[C:17]([CH3:18])[C:12]=2[O:11][C:10]1([CH3:36])[CH3:35].C([SiH](CC)CC)C>>[CH3:35][C:10]1([CH3:36])[CH:9]([C:37]2[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=2)[C:13]2[C:14]([CH3:34])=[C:15]([N:20]3[CH2:21][CH2:22][N:23]([C:26]4[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=4)[CH2:24][CH2:25]3)[C:16]([CH3:19])=[C:17]([CH3:18])[C:12]=2[O:11]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 102778831-(3-Hydroxy-2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazine

Product 1

HCID 102989121-(2,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazineYield 80%

Procedure

To trifluoroacetic acid was added 1-(3-hydroxy-2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazine (350 mg, 0.72 mmol) obtained in Example 33 (3.5 mL) under ice cooling. The mixture was warmed to room temperature, and then triethylsilane (0.3 mL, 1.9 mmol) was added at room temperature. The mixture was stirred for 15 minutes and concentrated under reduced pressure. The residue was made to basic with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic extract was washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was crystallized from hexane to obtain 270 mg (yield 80%) of the title compound. mp. 189–191° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-e5ffa29064794063bc4034c8b31f10c9
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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