Triethylamine → HCID 20205736, compound

HRID 1380204Notes

Reaction equation

HRID 1380204 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]=[O:12])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[ClH:13].Cl.Cl.[NH2:16][CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][N:23]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[CH2:22][CH2:21]1.C(N(CC)CC)C>C(Cl)Cl>[OH2:3].[OH2:3].[ClH:33].[ClH:13].[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][N:23]2[CH2:22][CH2:21][N:20]([CH2:19][CH2:18][CH2:17][NH:16][C:11]([NH:10][C:7]3[CH:8]=[CH:9][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][CH:6]=3)=[O:12])[CH2:25][CH2:24]2)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 994524-Acetylphenyl isocyanateHCID 202057391-(3-Aminopropyl)-4-(4-chlorobenzyl)piperazine trihydrochloride

Product 1

HCID 20205736HCID 20205736, compoundYield 230.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-acetylphenyl isocyanate (1.61 g; 10 mmole) in methylene chloride (100 ml) was added to a solution of 1-(3-aminopropyl)-4-(4-chlorobenzyl)piperazine trihydrochloride (3.77 g; 10 mmole), methylene chloride (50 ml) and triethylamine (4.3 ml; 31 mmole). The resulting mixture was refluxed 3 hours, washed with aqueous sodium bicarbonate, dried (sodium sulfate), and the product precipitated with ethereal hydrochloric acid. Recrystallization from ethanol provided the title compound (4.13 g; 82% yield) as a white powder, m.p. >197° C. (slow dec.).

Workup

  1. temperatureThe resulting mixture was refluxed 3 hours
  2. washwashed with aqueous sodium bicarbonate
  3. dry with materialdried (sodium sulfate)
  4. customthe product precipitated with ethereal hydrochloric acid
  5. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-03f0580f8a1d41d28f04c79b4fb671c1
Source dataset
uspto-grants-1986_04
Patent number
US04579947

Reaction notes

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