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

HRID 1380198Notes

Reaction equation

HRID 1380198 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:7].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:18][CH:17]=1.C(N(CC)CC)C>CCOCC>[ClH:1].[ClH:15].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][N:25]2[CH2:26][CH2:27][N:28]([CH2:2][CH2:3][CH2:4][NH:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:7])[CH2:29][CH2:30]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1628731-(3-(4-Chlorophenyl)propyl)piperazineHCID 136067321-(3-Chloropropyl)-3-n-hexylurea

Product 1

HCID 136067251-{3-[4-[3-(4-Chlorophenyl)propyl]piperazin-1-yl]-propyl}-3-n-hexylurea dihydrochlorideYield 64.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1-(3-chloropropyl)-3-n-hexylurea (2.21 g; 10 mmole), 1-[3-(4-chlorophenyl)propyl]piperazine (2.39 g; 10 mmole), triethylamine (1.01 g; 10 mmole) and alcohol (25 ml) was refluxed for 18 hours. The cooled reaction mixture was diluted with ether and washed with water, dried (sodium sulfate) and concentrated in vacuo. The resulting yellow viscous oil was purified on a silica gel column (methylene chloride/methanol; 93:7) and precipitated with ethereal hydrochloric acid to provide the title compound (1.6 g; 38% yield) as colorless crystals, m.p. 213°-216° C.

Workup

  1. temperaturewas refluxed for 18 hours
  2. customThe cooled reaction mixture
  3. washwashed with water
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customThe resulting yellow viscous oil was purified on a silica gel column (methylene chloride/methanol; 93:7)
  7. customprecipitated with ethereal hydrochloric acid

Sources & evidence

ORD record
ord-f311854efdbd49e0a98586968b38e346
Source dataset
uspto-grants-1986_04
Patent number
US04579947

Reaction notes

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