Methyl Isocyanate → 1-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-methylurea dihydrochloride

HRID 1380175Notes

Reaction equation

HRID 1380175 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:7][CH2:6]1.[CH3:19][N:20]=[C:21]=[O:22]>C(Cl)Cl>[ClH:18].[ClH:18].[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][N:8]2[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][CH2:2][NH:1][C:21]([NH:20][CH3:19])=[O:22])[CH2:6][CH2:7]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 13606667HCID 13606667, compound

Product 1

HCID 136066711-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-methylurea dihydrochlorideYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(3-aminopropyl)-4-(4-chlorobenzyl)piperazine (2.68 g; 10 mmole) and methyl isocyanate (0.57 g; 10 mmole) in methylene chloride (10 ml) was stirred at room temperature overnight. The reaction mixture was evaporated under reduced pressure, and the residue was chromatographed on a silica gel column (1"×24") using a methanolammonium hydroxide gradient (3-6%) with methylene chloride as the eluant. The product (1.0 g; 31% yield) was dissolved in methylene chloride/ether (1:1, 20 ml), and the solution was treated with anhydrous hydrogen chloride to precipitate the title compound as colorless crystals, m.p. 193°-207° C. (decomp.).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customthe residue was chromatographed on a silica gel column (1"×24")
  3. dissolutionThe product (1.0 g; 31% yield) was dissolved in methylene chloride/ether (1:1, 20 ml)
  4. additionthe solution was treated with anhydrous hydrogen chloride
  5. customto precipitate the title compound as colorless crystals, m.p. 193°-207° C. (decomp.)

Sources & evidence

ORD record
ord-3eba3cb675874705855b63b2a83bda92
Source dataset
uspto-grants-1986_04
Patent number
US04579947

Reaction notes

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