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

HRID 437236Notes

Reaction equation

HRID 437236 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 and ether 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 and ether
  3. customdried

Sources & evidence

ORD record
ord-a573edf98c094f8e8fcbc186544096e3
Source dataset
uspto-grants-1977_06
Patent number
US04029801

Reaction notes

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