Buchwald–Hartwig amination: 2-Chlorothiophene → 1-Boc-4-(2-thienyl)piperazine
0% yield, run at 95 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 2-Chlorothiophene | C₄H₃ClS | |
| Reactant | tert-Butyl piperazine-1-carboxylate | C₉H₁₈N₂O₂ | |
| Reagent | Triethylamine | C₆H₁₅N | |
| Catalyst | Triphenylphosphine | C₁₈H₁₅P | |
| Catalyst | Tetrakis(triphenylphosphine)palladium | C₇₂H₆₀P₄Pd | |
| Solvent | Dimethylformamide | C₃H₇NO | |
| Product | 1-Boc-4-(2-thienyl)piperazine | C₁₃H₂₀N₂O₂S | 0% |
Conditions
- Temperature
- 95 °C
Yield
- 0% of 1-Boc-4-(2-thienyl)piperazine.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
- Methyl 4-(4-Boc-1-piperazinyl)-2-chlorobenzoate91%
- Tert-butyl 4-(7-benzo[b]furanyl)piperazine-1-carboxylate84%
- Tert-butyl 4-(2-methylpyridin-3-yl)piperazine-1-carboxylate83%
- Tert-butyl 4-(4-cyanophenyl)piperazine-1-carboxylate82%
- Tert-butyl 4-(5-(benzyloxy)pyridin-2-YL)piperazine-1-carboxylate69%
- tert-Butyl 4-(2-(ethoxycarbonyl)benzofuran-4-yl)piperazine-1-carboxylate64%
- Tert-butyl 4-(2-methoxyphenyl)piperazine-1-carboxylate62%
- tert-butyl 4-(2-methyl-3-oxo-1H-isoindol-5-yl)piperazine-1-carboxylate57%
- Tert-butyl 4-(4-acetylphenyl)piperazine-1-carboxylate52%
- Tert-butyl 4-(3-chloro-4-cyanophenyl)piperazine-1-carboxylate47%
- tert-Butyl 4-(quinolin-2-yl)piperazine-1-carboxylate46%
- Tert-butyl 4-[6-[(4-methylsulfonylphenyl)methoxy]-3-pyridinyl]piperazine-1-carboxylate43%
Procedure
Copied from the source record, unedited
To a mixture of 2-chlorothiophene (0.248 mL, 2.68 mmol), tert-butyl piperazine-1-carboxylate (500 mg, 2.68 mmol), and TEA (1.123 mL, 8.05 mmol) in DMF (4 mL) was added Pd(Ph3P)4 (57.8 mg, .05 mmol). The reaction was allowed to heat at 95 °C for overnight. LCMS and TLC showed the starting material peak as well as the triphenyl phosphene ionized M+1 peak. The tryphenyl phosphene showed up at the same retention time as 2-chlorothiophene. No new peak was observed following the reaction so no purification techniques were run. MS (m+1) = not seen
The source
This record comes from experimental reaction archive (ord-37aa4a46f5494844887cf9e7ccaf1b0d). Open the source and check it against what is on this page.
experimental reaction archive record ord-37aa4a46f5494844887cf9e7ccaf1b0d from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.
How to read this record
This is one experiment, not a rule. It says that on one occasion these species were combined under these conditions and this came out. It does not say the reaction will give the same result on your substrate, and nothing on the page has been generalised into a claim that it would.
The pathway is a separate question, kept on separate pages. A mechanism here is the canonical arrow pushing for a class, run on real structures and labelled rule-derived. It is not evidence, and this record is not a mechanism.
Where to next
More Buchwald–Hartwig amination records
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