HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → (S)-2-Benzyl-4-(4-bromo-benzyl)-1-methyl-piperazine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 3-(S)-benzyl-1-(4-bromobenzyl)-piperazine | HCID 57849462 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | (S)-2-Benzyl-4-(4-bromo-benzyl)-1-methyl-piperazine | HCID 57849477 | 82% |
Reaction Steps
To a solution of 369 mg of 3-(S)-benzyl-1-(4-bromobenzyl)-piperazine in 3 mL of tetrahydrofuran was added 0.8 mL of formaldehyde and 0.15 mL acetic acid. After 2 h, 453 mg of sodium triacetoxyborohydride was added and the reaction was stirred overnight. Diluted carefully with aqueous saturated sodium bicarbonate solution and extracted with ethyl acetate. The combined organics were washed with brine, dried with sodium sulfate, filtered and concentrated in vacuo. Used crude in subsequent reactions. 82% yield. ES MS (+)m/z 361
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07595397B2 |
| Source dataset | uspto-grants-2009_09 |
| ORD ID | ord-fd0787d7fff346f0a83885ddd409c5f9 |
| Source note | uspto-grants-2009_09 |