Triethylamine → HCID 19776676, compound

HRID 1612754Notes

Reaction equation

HRID 1612754 reaction equation
[C:1]1([CH2:7][CH:8]2[CH2:13][CH2:12][CH2:11][NH:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30](Cl)=[O:31])=[CH:25][CH:24]=1>O1CCCC1>[C:1]1([CH2:7][CH:8]2[CH2:13][CH2:12][CH2:11][N:10]([C:30](=[O:31])[CH2:29][C:26]3[CH:27]=[CH:28][C:23]([O:22][CH3:21])=[CH:24][CH:25]=3)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1145513-BenzylpiperidineHCID 27346884-Methoxyphenylacetyl chloride

Product 1

HCID 19776676HCID 19776676, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the 3-phenylmethylpiperidine (1.75 g, 10 mmol) obtained in Example 1 (ii) and triethylamine (2.1 ml, 15 mmol) in tetrahydrofuran (10 ml) at 0° C. was added dropwise a solution of 4-methoxyphenylacetyl chloride (2.21 g, 12 mmol) in tetrahydrofuran (10 ml). The resultant mixture was stirred for 2 hours and the precipitate filtered off. The filtrate was then washed with saturated aqueous sodium bicarbonate (5 ml), dried with sodium sulphate and evaporated in vacuo. The residue was purified by flash column chromatography on silica gel using 1:1 then 2:1 ethyl acetate: hexane as eluant to give 3-phenylmethyl-N-(4'-methoxyphenyl)acetylpiperidine as a light yellow syrup (2.23 g), M+ found: 324.

Workup

  1. filtrationthe precipitate filtered off
  2. washThe filtrate was then washed with saturated aqueous sodium bicarbonate (5 ml)
  3. dry with materialdried with sodium sulphate
  4. customevaporated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel using 1:1

Sources & evidence

ORD record
ord-edcb9bf1324241e5998388781d28478e
Source dataset
uspto-grants-1993_03
Patent number
US05190958

Reaction notes

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