Trifluoroacetic acid → HCID 9909244, compound

HRID 1736089Notes

Reaction equation

HRID 1736089 reaction equation
FC(F)(F)C(O)=O.[N:8]1([C:14]2[CH:37]=[CH:36][C:17]3[C:18]([CH2:21][CH2:22][CH:23]4[CH2:28][CH2:27][N:26]([C:29](OC(C)(C)C)=O)[CH2:25][CH2:24]4)=[N:19][O:20][C:16]=3[CH:15]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[C:38]1(SC)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C(N(CC)CC)C.C(Br)C1C=CC=CC=1>C(Cl)Cl>[N:8]1([C:14]2[CH:37]=[CH:36][C:17]3[C:18]([CH2:21][CH2:22][CH:23]4[CH2:28][CH2:27][N:26]([CH2:29][C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)[CH2:25][CH2:24]4)=[N:19][O:20][C:16]=3[CH:15]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 7498Benzyl BromideHCID 7520ThioanisoleHCID 8471TriethylamineHCID 10432013HCID 10432013, compound

Product 1

HCID 9909244HCID 9909244, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic acid (TFA) (5 mL) was added to a cold (0° C.) solution of the piperidine formed in step b (0.40 g, 0.96 mmol) and thioanisole (1.13 mL, 9.60 mmol) in CH2Cl2 (10 mL). The resulting mixture was stirred at 0° C. for 30 min. Volatiles were removed under reduced pressure and 1N sodium hydroxide (NaOH) was added to the residue. The aqueous layer was extracted with EtOAc (2 times) and the combined organic layer was washed with water and brine and dried (MgSO4), filtered, and concentrated. The yellow oil obtained was redissolved in CH2Cl2 (10 mL), and triethylamine (0.267 mL, 1.92 mmol) and benzyl bromide (0.148 mL, 1.25 mmol) were added. The resulting mixture was stirred overnight at room temperature. The mixture was washed with water and brine and dried (MgSO4), filtered, and concentrated. Purification by silica gel flash chromatography (CH2Cl2 →10% MeOH/CH2Cl2) gave the title compound (0.285 g, 73%) as a white solid. A small sample was further purified by recrystallization (EtOH) to give a white solid.

Workup

  1. customVolatiles were removed under reduced pressure and 1N sodium hydroxide (NaOH)
  2. additionwas added to the residue
  3. extractionThe aqueous layer was extracted with EtOAc (2 times)
  4. washthe combined organic layer was washed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe yellow oil obtained
  9. stirringThe resulting mixture was stirred overnight at room temperature
  10. washThe mixture was washed with water and brine
  11. dry with materialdried (MgSO4)
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customPurification by silica gel flash chromatography (CH2Cl2 →10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-d2a61e6a4dcc4d609553255cd0b658d4
Source dataset
uspto-grants-1996_07
Patent number
US05538984

Reaction notes

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