Triethylamine → 1-(3-Phenylpropionyl)-3-(3-methoxyphenyl)piperidine

HRID 1731886Notes

Reaction equation

HRID 1731886 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.[C:22]1([CH2:28][CH2:29][C:30](Cl)=[O:31])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1(C)C=CC=CC=1.C(OCC)C>[C:22]1([CH2:28][CH2:29][C:30]([N:11]2[CH2:12][CH2:13][CH2:14][CH:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:10]2)=[O:31])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 64801Benzenepropanoyl chlorideHCID 110742303-(3-Methoxyphenyl)piperidine

Product 1

HCID 136049031-(3-Phenylpropionyl)-3-(3-methoxyphenyl)piperidineYield 148.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 9.4 g (49.2 mmole) of 3-(3-methoxyphenyl)piperidine and 10.2 ml (73.8 mmole) of triethylamine in 120 ml of toluene, at 0° C., under nitrogen, was added dropwise, a solution of 12.4 g (73.8 mmole) of 3-phenylpropionyl chloride in 45 ml of toluene. The mixture was allowed to warm to room temperature, and then it was diluted with an equal volume of diethyl ether. The solid was removed by filtration and the filtrate was evaporated in vacuo to give 23.7 g of 1-(3-phenylpropionyl)-3-(3-methoxyphenyl)piperidine.

Workup

  1. customThe solid was removed by filtration
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-ea3879e972df4b3caf0840b3274b4cbf
Source dataset
uspto-grants-1986_11
Patent number
US04623728

Reaction notes

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