Triethylamine → 1-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-[4-(methylthio)phenyl]urea dihydrochloride monohydrate

HRID 543193Notes

Reaction equation

HRID 543193 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[O:11])=[CH:5][CH:4]=1.[ClH:12].Cl.Cl.[NH2:15][CH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[CH2:21][CH2:20]1.C(N(CC)CC)C>C(Cl)Cl>[OH2:11].[ClH:32].[ClH:12].[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][N:22]2[CH2:21][CH2:20][N:19]([CH2:18][CH2:17][CH2:16][NH:15][C:10]([NH:9][C:6]3[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=3)=[O:11])[CH2:24][CH2:23]2)=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27333164-(Methylthio)phenyl isocyanateHCID 202057391-(3-Aminopropyl)-4-(4-chlorobenzyl)piperazine trihydrochloride

Product 1

HCID 202057641-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-[4-(methylthio)phenyl]urea dihydrochloride monohydrateYield 172.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The procedure described in Example 29 was followed, using 4-(methylthio)phenyl isocyanate (10.0 g; 60.5 mmole), 1-(3-aminopropyl)-4-(4-chlorobenzyl)piperazine trihydrochloride (22.8 g; 60.5 mmole), methylene chloride (400 ml), and triethylamine (25.8 ml; 185 mmole). Recrystallization from methanol/water provided the title compound (27.3 g; 89% yield) as colorless crystals, m.p. 212°-214° C.

Workup

  1. customRecrystallization from methanol/water

Sources & evidence

ORD record
ord-8ecbcafe8040401bb34a70ddb69c4c7d
Source dataset
uspto-grants-1987_04
Patent number
US04661481

Reaction notes

Loading…