HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 223
Notes
Print preview

Reaction equation

HRID 223 reaction equation
Brc1ccccc1.CC(C)(C)OC(=O)NCCC1CCNCC1>CC(=O)O.CC(=O)O.CC(C)(C)[O-].CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.Cc1ccccc1.[Na+].[Pd]>CC(C)(C)OC(=O)NCCC1CCN(c2ccccc2)CC1
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 7961BromobenzeneHCID 15018494-(2-Aminoethyl)piperidine, 4-BOC protected

Product 1

HCID 69152784tert-butyl N-[2-(1-phenylpiperidin-4-yl)ethyl]carbamateYield 0%

Reagents, catalysts & solvents 4

HCID 23676156Sodium t-butoxideReagentHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)
Catalyst
HCID 4144353Palladium (II) acetateCatalyst
HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

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.

Sources & evidence

ORD record
ord-59ade4a657944ddaa87cf04392b14d28
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureSources & evidenceReaction notes