Potassium Carbonate → 1-[2-(3,4-Dichlorophenyl)ethyl]-4-benzamidopiperidine

HRID 1730347Notes

Reaction equation

HRID 1730347 reaction equation
[C:1]([NH:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:22][C:23]1[CH:24]=[C:25]([CH2:30][CH2:31]Br)[CH:26]=[CH:27][C:28]=1[Cl:29]>>[Cl:22][C:23]1[CH:24]=[C:25]([CH2:30][CH2:31][N:13]2[CH2:14][CH2:15][CH:10]([NH:9][C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:11][CH2:12]2)[CH:26]=[CH:27][C:28]=1[Cl:29]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 118120N-4-PiperidylbenzamideHCID 151493894-(2-Bromoethyl)-1,2-dichlorobenzene

Product 1

HCID 214132531-[2-(3,4-Dichlorophenyl)ethyl]-4-benzamidopiperidineYield 94.2%

Conditions

Temperature
100 °C

Procedure

4-Benzamidopiperidine (204 mg.) and anhydrous potassium carbonate (138 mg.)were intimately ground together and added to 2-(3,4-dichlorophenyl)ethyl bromide (254 mg.). The resulting paste was heated at 100° C for 2 hours to give a hard solid. This was broken up, washed well with water andether and dried to give the title compound (355 mg.). Recrystallisation from ethanolic hydrogen chloride and ether gave the hydrochloride (237 mg.), m.p. 286.0° C. (Found: C, 58.2; H, 5.8; N, 6.8. C20H22Cl2N2O.HCl requires C, 58.05; H, 5.6; N, 6.8%).

Workup

  1. customto give a hard solid
  2. washwashed well with water andether
  3. customdried

Sources & evidence

ORD record
ord-dc49b45bbee1484b94c8efa1040cbaa0
Source dataset
uspto-grants-1976_11
Patent number
US03992389

Reaction notes

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