Triethylamine → 1-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-n-hexylurea dihydrochloride

HRID 543164

Reaction equation

HRID 543164 reaction equation
[ClH:1].Cl.Cl.[NH2:4][CH2:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1.C(N(CC)CC)C.[CH2:29]([N:35]=[C:36]=[O:37])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>O1CCCC1>[ClH:21].[ClH:1].[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][N:11]2[CH2:12][CH2:13][N:8]([CH2:7][CH2:6][CH2:5][NH:4][C:36]([NH:35][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:37])[CH2:9][CH2:10]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75659Hexyl isocyanateHCID 202057391-(3-Aminopropyl)-4-(4-chlorobenzyl)piperazine trihydrochloride

Product 1

HCID 136066751-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-n-hexylurea dihydrochlorideYield 171%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure described in Example 3 was followed, using 1-(3-aminopropyl)-4-(4-chlorobenzyl)piperazine trihydrochloride (3.77 g; 10 mmole), tetrahydrofuran (50 ml), triethylamine (4.2 ml; 30 mmole) and n-hexyl isocyanate (1.41 g; 10 mmole). Recrystallization from ethanol provided the title compound (4.00 g; 83% yield) as colorless crystals, m.p. 214°-215° C.

Workup

  1. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-5dce3f3f78324982a5731e453336c4cf
Source dataset
uspto-grants-1987_04
Patent number
US04661481

Linked notes

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