Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Thiophosgene | HCID 10040 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 4-((4-Methylpiperazin-1-yl)methyl)aniline | HCID 3153996 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86624312 | HCID 86624312 | 73.1% |
Reaction Steps
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%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08399464B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-5fc5635dd0324c4d81d536da3c453888 |
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| Source note | uspto-grants-2013_03 |
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