Triethylamine → HCID 86734517, compound

HRID 596192Notes

Reaction equation

HRID 596192 reaction equation
[Cl:1][C:2]([N:4]1[C:10]2[S:11][C:12]([CH2:14][CH3:15])=[CH:13][C:9]=2[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])=[N:7][CH2:6][CH2:5]1)=[O:3].C(N(CC)CC)C.[CH3:30][N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>C1(C)C=CC=CC=1>[ClH:1].[ClH:1].[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:8]1[C:9]2[CH:13]=[C:12]([CH2:14][CH3:15])[S:11][C:10]=2[N:4]([C:2]([N:34]2[CH2:35][CH2:36][N:31]([CH3:30])[CH2:32][CH2:33]2)=[O:3])[CH2:5][CH2:6][N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 21451001HCID 21451001, compound

Product 1

HCID 86734517HCID 86734517, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 12.0 g of 1-chlorocarbonyl-5-o-chlorophenyl-7-ethyl-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepine and 3.8 g of triethylamine in 50 ml of toluene is added dropwise a solution of 3.8 g of N-methylpiperazine in 10 ml of toluene with stirring. The whole solution is refluxed with stirring for 30 minutes, and then cooled. The precipitated triethylamine hydrochloride is filtered off. After the filtrate is washed with water and dried over anhydrous magnesium sulfate, the solvent is evaporated under reduced pressure. The residue is treated with ethanolic hydrogen chloride to give 5-o-chlorophenyl-7-ethyl-1-(4-methyl-1-piperazinylcarbonyl)-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepine dihydrochloride 1/2 -hydrate as yellow crystals. This product, when recrystallized from acetone containing water, melts at 248°-250° C with decomposition.

Workup

  1. temperatureThe whole solution is refluxed
  2. stirringwith stirring for 30 minutes
  3. temperaturecooled
  4. filtrationThe precipitated triethylamine hydrochloride is filtered off
  5. washAfter the filtrate is washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent is evaporated under reduced pressure
  8. additionThe residue is treated with ethanolic hydrogen chloride

Sources & evidence

ORD record
ord-3c346ccfac584d148c42d5bd4fa8a875
Source dataset
uspto-grants-1977_03
Patent number
US04010184

Reaction notes

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