N,N-Dimethylethylenediamine → 4-(4-Chlorophenyl)-N-[2-(dimethylamino)ethyl]-1-piperazinecarboxamide

HRID 1087825Notes

Reaction equation

HRID 1087825 reaction equation
[CH3:1][N:2]([CH3:21])[CH2:3][CH2:4][NH:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17](F)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7].C(N1C=CN=C1)(N1C=CN=C1)=O.CN(CCN)C.[Cl:40]C1C=CC(N2CCNCC2)=CC=1>O1CCCC1>[Cl:40][C:17]1[CH:18]=[CH:19][C:14]([N:11]2[CH2:12][CH2:13][N:8]([C:6]([NH:5][CH2:4][CH2:3][N:2]([CH3:21])[CH3:1])=[O:7])[CH2:9][CH2:10]2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 66053N,N-DimethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 974781-(4-Chlorophenyl)piperazineHCID 14763463N-[2-(Dimethylamino)ethyl]-4-(4-fluorophenyl)-1-piperazinecarboxamide

Product 1

HCID 147634684-(4-Chlorophenyl)-N-[2-(dimethylamino)ethyl]-1-piperazinecarboxamideYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound was prepared according to the procedure used to synthesize the compound of Example 11. A mixture of 4.9 g (0.03 mole) of 1,1'-carbonyldiimidazole, 2.6 g (0.03 mole) of unsym-dimethylethylenediamine, and 5.9 g (0.03 mole) of 1-(4-chlorophenyl)piperazine in a total of 200 ml of tetrahydrofuran gave an oil which solidified when triturated with petroleum ether (30°-60° C.). The collected solid was recrystallized from 2-propanol-isopropyl ether to yield 6.1 g (66%) of the title compound as a white, crystalline solid, m.p. 125°-128° C.

Workup

  1. customThis compound was prepared
  2. customgave an oil which
  3. customtriturated with petroleum ether (30°-60° C.)
  4. customThe collected solid was recrystallized from 2-propanol-isopropyl ether

Sources & evidence

ORD record
ord-196cf5f3790c41b18a0b7005bd77952a
Source dataset
uspto-grants-1990_10
Patent number
US04960776

Reaction notes

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