Triethylamine → HCID 86624312, compound

HRID 1947208Notes

Reaction equation

HRID 1947208 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)[CH2:11][CH2:10]1.[C:23](Cl)(Cl)=[S:24].C(=O)([O-])O.[Na+]>O1CCCC1>[N:22]([C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:12]2[CH2:13][CH2:14][N:9]([CH3:8])[CH2:10][CH2:11]2)=[CH:17][CH:18]=1)=[C:23]=[S:24]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 31539964-((4-Methylpiperazin-1-yl)methyl)aniline

Product 1

HCID 86624312HCID 86624312, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (5.1 mL, 36.6 mmol) was added to a solution of 4-(4-methylpiperazin-1-ylmethyl)phenylamine (F652-02, 3.14 g, 15.3 mmol) in tetrahydrofuran (250 mL), and after cooling by ice, thiophosgene (1.11 mL, 14.6 mmol) was added. After stirring at room temperature overnight, aqueous sodium hydrogencarbonate was added to the mixture. The reaction mixture was extracted with ethyl acetate, and the extract was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered to remove sodium sulfate, and the solvent was distilled off under reduced pressure to obtain brown oil. The brown oil was purified by silica gel column chromatography (chloroform, methanol) to obtain 1-(4-isothiocyanatobenzyl)-4-methylpiperazine (F652-03, brownish oil, 2.64 g, 70%).

Workup

  1. additionwas added
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washthe extract was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customto remove sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customto obtain brown oil
  9. customThe brown oil was purified by silica gel column chromatography (chloroform, methanol)

Sources & evidence

ORD record
ord-5fc5635dd0324c4d81d536da3c453888
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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