Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | HCID 59588794 | HCID 59588794 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 23728855 | HCID 23728855 | 50.2% |
Reaction Steps
To a solution of 2-(4-cyclopropylpiperazin-1-yl)benzothiazole-6-carboxaldehyde (500 mg, 1.7 mmol) in MeOH (14 mL) and THF (28 mL) was added morpholine (296 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, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by preparative HPLC to give 306 mg (31%) of 2-(4-cyclopropylpiperazin-1-yl)-6-(morpholin-4-ylmethyl)-benzothiazole as a trifluoroacetate salt.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08394842B2 |
|---|
| Source dataset | uspto-grants-2013_03 |
|---|
| ORD ID | ord-164716f3dd144264b3090f6371893476 |
|---|
| Source note | uspto-grants-2013_03 |
|---|