Dibenzylamine → HCID 21430476, compound

HRID 437164Notes

Reaction equation

HRID 437164 reaction equation
Cl.[CH3:2][N:3]([CH3:23])[S:4]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[N:16]1[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]1)[C:10](Cl)=[O:11])(=[O:6])=[O:5].[CH2:24]([NH:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>O1CCCC1.[OH-].[Na+]>[CH2:32]([N:31]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:10](=[O:11])[C:9]1[CH:13]=[CH:14][C:15]([N:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)=[C:7]([S:4](=[O:6])(=[O:5])[N:3]([CH3:23])[CH3:2])[CH:8]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 7656DibenzylamineHCID 8471TriethylamineHCID 21430472HCID 21430472, compound

Product 1

HCID 21430476HCID 21430476, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

40 Grams of 3-dimethylsulfamoyl-4-(4-methylpiperazine-1-yl)-benzoylchloride-hydrochloride (0.1 mole) were added portionwise at room temperature, while stirring, to a solution of 22 g of dibenzylamine and 20 g of triethylamine in 0.2 l of tetrahydrofurane. Subsequently the reaction mixture was heated for another hour under reflux, and then the tetrahydrofurane was eliminated in vacuo. The amorphous residue was dispersed in 0.5 l of acetic ester and 0.5 l of 1N NaOH. The acetic ester phase was separated and was dried over magnesium sulfate. The acetic ester solution was then concentrated to half its volume and was mixed with the same volume of petroleum ether under heat. Upon trituration the final product crystallized and was suction-filtered after having been cooled with ice water for 1 hour.

Workup

  1. temperatureSubsequently the reaction mixture was heated for another hour
  2. temperatureunder reflux
  3. customThe acetic ester phase was separated
  4. dry with materialwas dried over magnesium sulfate
  5. concentrationThe acetic ester solution was then concentrated to half its volume
  6. additionwas mixed with the same volume of petroleum ether
  7. temperatureunder heat
  8. customUpon trituration the final product crystallized
  9. filtrationwas suction-filtered
  10. temperatureafter having been cooled with ice water for 1 hour

Sources & evidence

ORD record
ord-f7e6452a9cd543729bb40f880e0fb7a0
Source dataset
uspto-grants-1977_06
Patent number
US04029787

Reaction notes

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