1-(2-Chloroethyl)-4-phenylpiperazine dihydrochloride → 5-Benzyloxy-2-(2-[4-phenyl-1-piperazinyl]ethylamino)benzamide

HRID 1439609Notes

Reaction equation

HRID 1439609 reaction equation
Cl.Cl.Cl[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7]1.[CH2:18]([O:25][C:26]1[CH:34]=[C:30]([C:31]([NH2:33])=[O:32])[C:29]([NH2:35])=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)CC>[CH2:18]([O:25][C:26]1[CH:27]=[CH:28][C:29]([NH:35][CH2:4][CH2:5][N:6]2[CH2:11][CH2:10][N:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:8][CH2:7]2)=[C:30]([CH:34]=1)[C:31]([NH2:33])=[O:32])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 117380551-(2-Chloroethyl)-4-phenylpiperazine dihydrochlorideHCID 203381422-Amino-5-(benzyloxy)benzamide

Product 1

HCID 203384875-Benzyloxy-2-(2-[4-phenyl-1-piperazinyl]ethylamino)benzamideYield 29.5%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

1-(2-Chloroethyl)-4-phenylpiperazine dihydrochloride (3.3 g) was converted to the base and added to 1.2 g 5-Benzyloxyanthranilamide in 125 ml propanol. The solution was refluxed 3 hours, cooled, filtered, and the filtrate concentrated to dryness. The residue was chromatographed on alumina to give 0.63 g product.

Workup

  1. temperatureThe solution was refluxed 3 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated to dryness
  5. customThe residue was chromatographed on alumina

Sources & evidence

ORD record
ord-c8ef1edc2f7840eda1b4d8fd7788ec77
Source dataset
uspto-grants-1977_11
Patent number
US04060526

Reaction notes

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