HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-(Bromomethyl)thiophene → 4-[(4-Cyano-phenyl)-thiophen-3-ylmethyl-amino]-piperidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-(Bromomethyl)thiophene | HCID 520703 | — |
| Reactant | Potassium bis(trimethylsilyl)amide | HCID 3251421 | — |
| Reactant | 1-Boc-4-[(4-cyanophenyl)amino]-piperidine | HCID 18539207 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-[(4-Cyano-phenyl)-thiophen-3-ylmethyl-amino]-piperidine-1-carboxylic acid tert-butyl ester | HCID 68970643 | 61% |
Reaction Conditions
| Temperature | -78 °C |
|---|
Reaction Steps
To a solution of 4-(4-cyano-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (see EXAMPLE 106) (1.17 g, 3.89 mmol) in THF (20 mL) cooled to −78° C. was added KHMDS (0.5M, 12.0 mL, 6.0 mmol) and the mixture was stirred at −78° C. for 20 minutes. The reaction was quenched with 3-(bromomethyl)thiophene (1.06 g, 5.99 mmol) and warmed to room temperature to afford 4-[(4-cyano-phenyl)-thiophen-3-ylmethyl-amino]-piperidine-1-carboxylic acid tert-butyl ester (941 mg, 61%) following work-up and purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07491735B2 |
| Source dataset | uspto-grants-2009_02 |
| ORD ID | ord-ea0a9ac3c5ae45daa88e2163116b0a6f |
| Source note | uspto-grants-2009_02 |