Carbon Tetrachloride → N-3-[4-(2-chlorophenyl)piperazin-1-yl]propyl-N'-(3,4-ethylenedioxyphenyl)carbodiimide

HRID 5860Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]3[O:27][CH2:28][CH2:29][O:30][C:23]=3[CH:22]=2)=S)[CH2:10][CH2:9]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][N:17]=[C:18]=[N:20][C:21]2[CH:26]=[CH:25][C:24]3[O:27][CH2:28][CH2:29][O:30][C:23]=3[CH:22]=2)[CH2:12][CH2:13]1

Participants

Conditions

Temperature: 400 °C

Procedure

A mixture of N-3-[4-(2-chlorophenyl)piperazin-1-yl]propyl-N '-(3,4-ethylenedioxyphenyl)thiourea of Example 11 (1.35 g; 3 mmol), triphenylphosphin (1.02 g; 3.9 mmol), carbon tetrachloride (0.56 ml), triethylamine (0.3 g; 3 mmol) and methylene chloride (15 ml) Was stirred at reflux for 3 h and at 400° C. for 16 h. The reaction mixture was concentrated in vacuo and then taken up in petroleum ether. The solution was filtered and concentrated in vacuo to give 0.7 g N-3-[4-(2-chlorophenyl)piperazin-1-yl]propyl-N'-(3,4-ethylenedioxyphenyl)carbodiimide as an oil.

Workup

concentrationThe reaction mixture was concentrated in vacuo
filtrationThe solution was filtered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b2cfaed8d84f496bad77a7ddcfae135c
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05246935

Reaction notes

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