Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Dimethylamine, hydrochloride | HCID 10473 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | HCID 59588794 | HCID 59588794 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 23728854 | HCID 23728854 | 68.2% |
Reaction Steps
To a solution of 2-(4-cyclopropylpiperazin-1-yl)benzothiazole-6-carboxaldehyde (500 mg, 1.7 mmol) in methanol (14 mL) and THF (28 mL) was added dimethylamine hydrochloride (277 mg, 3.4 mmol), acetic acid (22 mg, 0.4 mmol) and NaCNBH3 (158 mg, 2.7 mmol). The mixture was stirred at 63° C. overnight. Then the resulting mixture was concentrated under reduced pressure and the residue was diluted with dichloromethane (15 mL). The mixture was washed with brine and the organic phase was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by preparative HPLC to give 367 mg (32%) of [2-(4-cyclopropylpiperazin-1-yl)benzothiazol-6-ylmethyl]dimethyl-amine as a trifluoroacetate salt.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08394842B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-d9225e0463114c26a24181749da5dce1 |
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| Source note | uspto-grants-2013_03 |
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