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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 223Generated: October 23, 2026

Bromobenzene → tert-butyl N-[2-(1-phenylpiperidin-4-yl)ethyl]carbamate

https://huagongshe.com/en/reaction/223

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBromobenzeneHCID 7961—
Reactant4-(2-Aminoethyl)piperidine, 4-BOC protectedHCID 1501849—
ReagentSodium t-butoxideHCID 23676156—
Catalyst1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 636044—
CatalystPalladium (II) acetateHCID 4144353—
SolventTolueneHCID 1140—
Producttert-butyl N-[2-(1-phenylpiperidin-4-yl)ethyl]carbamateHCID 691527840%

Reaction Conditions

Temperature50 °C

Reaction Steps

palladium(II) acetate (21.45 mg, 0.10 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (111 mg, 0.19 mmol) were placed in a round-bottomed vessel that was filled with nitrogen. Toluene (0.8 mL) was added and the mixture was heated to 50°C for 30 min. sodium tert-butoxide (138 mg, 1.43 mmol) was added to a second vessel and inerted with nitrogen. tert-butyl 2-(piperidin-4-yl)ethylcarbamate (342 mg, 1.5 mmol) and bromobenzene (150mg, 0.96 mmol) and toluene (1.4 mL) were added. 14/04 2009 13:57:24 +0200 The catalyst solution was added to the reagent mixture and the combined mixture was heated to reflux for several hours. The reaction did not work.

Provenance & Evidence

Source dataset750 AstraZeneca ELN dataset
ORD IDord-59ade4a657944ddaa87cf04392b14d28
Source note750 AstraZeneca ELN dataset