Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Diisobutylaluminum hydride | HCID 14487 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 4-(6-(4-Cyclopropylmethylpiperazin-1-yl)-pyridin-3-yl)-benzonitrile | HCID 58006667 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 58006707 | HCID 58006707 | 51% |
Reaction Steps
To a solution of 4-[6-(4-cyclopropylmethyl-piperazin-1-yl)-pyridin-3-yl]-benzonitrile (2.0 g 6.3 mmol) dissolved in THF (40 mL) was added DIBAL-H (25 mL, 1 N) at −40° C. The mixture was stirred 2 h at −40° C. and then CH3OH (15 mL), water (100 mL) and 1 N NaOH (15 mL) was added at −40° C. The mixture was extracted with EtOAc (3×300 mL). The combined organic extracts were washed with water (3×50 mL), dried (Na2SO4) and concentrated under reduced pressure to give 1.7 g (51%) of 4-[6-(4-cyclopropylmethyl-piperazin-1-yl)-pyridin-3-yl]-benzaldehyde.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08501739B2 |
|---|
| Source dataset | uspto-grants-2013_08 |
|---|
| ORD ID | ord-507f09ea240c4d9380b47e81459286d3 |
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| Source note | uspto-grants-2013_08 |
|---|
