N,N-Dimethylethylenediamine → N-[2-(Dimethylamino)ethyl]-4-(4-methylphenyl)-1-piperazinecarboxamide

HRID 1087830Notes

Reaction equation

HRID 1087830 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:22](N1C=CN=C1)(N1C=CN=C1)=O.CN(CCN)C.CC1C=CC(N2CCNCC2)=CC=1>O1CCCC1>[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]([CH3:22])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7]

Participants

6

Reactant 4

HCID 66053N,N-DimethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 831131-(p-Tolyl)piperazineHCID 14763463N-[2-(Dimethylamino)ethyl]-4-(4-fluorophenyl)-1-piperazinecarboxamide

Product 1

HCID 14763473N-[2-(Dimethylamino)ethyl]-4-(4-methylphenyl)-1-piperazinecarboxamideYield 47%

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 1.9 g (0.01 mole) of 1,1'-carbonyldiimidazole, 1.0 g (0.01 mole) of unsym-dimethylethylenediamine, and 2.0 g (0.1 mole) of 1-(4-methylphenyl)piperazine in a total volume of 100 ml of tetrahydrofuran gave an oil which solidified. The solid was triturated with petroleum ether (30°-60° C.) to give 1.5 g (47%) of the title compound as a white solid, m.p. 85°-88° C.

Workup

  1. customThis compound was prepared
  2. customgave an oil which
  3. customThe solid was triturated with petroleum ether (30°-60° C.)

Sources & evidence

ORD record
ord-db2258acc23c4caabec555c060e83785
Source dataset
uspto-grants-1990_10
Patent number
US04960776

Reaction notes

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