Trifluoroacetic acid → 4-[Bis(4-ethylphenyl)methyl]-1-[(4-methoxyphenyl)methyl]piperidine

HRID 866067Notes

Reaction equation

HRID 866067 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([C:16]([C:26]3[CH:31]=[CH:30][C:29]([CH2:32][CH3:33])=[CH:28][CH:27]=3)([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH3:25])=[CH:20][CH:19]=3)O)[CH2:12][CH2:11]2)=[CH:5][CH:4]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH:16]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH3:25])=[CH:20][CH:19]=3)[C:26]3[CH:31]=[CH:30][C:29]([CH2:32][CH3:33])=[CH:28][CH:27]=3)[CH2:12][CH2:11]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 19040923HCID 19040923, compound

Product 1

HCID 190409094-[Bis(4-ethylphenyl)methyl]-1-[(4-methoxyphenyl)methyl]piperidineYield 58.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1.0 gram (0.002 mole) of N-(4-methoxyphenylmethyl)-4-[bis(4-ethylphenyl)hydroxymethyl]piperidine (prepared in the manner of Example 1) in 10 mL of methylene chloride was slowly added 1.1 mL (0.007 mole) of triethylsilane, followed by 1.0 mL (0.013 mole) of trifluoroacetic acid. The reaction mixture was then stirred at ambient temperature during a five hour period. After this time the reaction mixture was neutralized with solid sodium carbonate. The mixture was then partitioned between 100 mL of methylene chloride and 50 mL of water. The organic layer was separated and washed with two 50 mL portions of an aqueous solution saturated with sodium chloride. The organic layer was then dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue, which was purified by subjecting it to preparative thin layer chromatography, with 25% acetone in methylene chloride as the eluant, yielding about 0.5 gram of N-(4-methoxyphenylmethyl)-4-[bis(4-ethylphenyl)methyl]piperidine. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThe mixture was then partitioned between 100 mL of methylene chloride and 50 mL of water
  2. customThe organic layer was separated
  3. washwashed with two 50 mL portions of an aqueous solution saturated with sodium chloride
  4. dry with materialThe organic layer was then dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure to a residue, which
  7. customwas purified

Sources & evidence

ORD record
ord-73138a1fbfd04fe79b4851aa4db5b1da
Source dataset
uspto-grants-1996_10
Patent number
US05569664

Reaction notes

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