Formic Acid → 4-(4-Phenoxyphenyl)-1-[(2,3,4-trimethoxyphenyl)methyl]piperidine

HRID 1004134Notes

Reaction equation

HRID 1004134 reaction equation
OC1C=CC(/C=C/C[N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)=CC=1OC.[CH3:32][O:33][C:34]1[C:41]([O:42][CH3:43])=[C:40]([O:44][CH3:45])[CH:39]=[CH:38][C:35]=1[CH:36]=O.C(O)=O.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[O:23]([C:20]1[CH:21]=[CH:22][C:17]([CH:14]2[CH2:13][CH2:12][N:11]([CH2:36][C:35]3[CH:38]=[CH:39][C:40]([O:44][CH3:45])=[C:41]([O:42][CH3:43])[C:34]=3[O:33][CH3:32])[CH2:16][CH2:15]2)=[CH:18][CH:19]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 750062,3,4-TrimethoxybenzaldehydeHCID 516892Sodium BicarbonateHCID 18412177(E)-1-[3-(4-hydroxy-3-methoxyphenyl)-2-propenyl]-4-(4-phenoxyphenyl)piperidine

Product 1

HCID 184121744-(4-Phenoxyphenyl)-1-[(2,3,4-trimethoxyphenyl)methyl]piperidineYield 73%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1.27 g of the compound (9) synthesized in Example 2 and 0.8 g of 2,3,4-trimethoxybenzaldehyde was stirred at 120° C., then, 0.18 ml of formic acid was added dropwise. This was stirred for one hour at the same temperature, then ethyl acetate and a saturated aqueous solution of sodium hydrogencarbonate were added and the results were shaken. The organic layer was dried, filtered, then concentrated under reduced pressure to obtain a residue which was then purified by silica gel column chromatography (hexane:ethyl acetate=3:2) to obtain the above-referenced compound (29) in an amount of 1.46 g (yield 73%).

Workup

  1. stirringThis was stirred for one hour at the same temperature
  2. stirringthe results were shaken
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto obtain a residue which
  7. customwas then purified by silica gel column chromatography (hexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-6a2c08da0e214461bd2ea539b5c5c2ac
Source dataset
uspto-grants-2000_04
Patent number
US06048876

Reaction notes

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