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

HRID 221

Reaction equation

HRID 221 reaction equation
CC(C)(C)OC(=O)NCCC1CCNCC1.Ic1ccccc1>CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.COCCOC.O=P([O-])([O-])[O-].[K+].[K+].[K+].[Pd]>CC(C)(C)OC(=O)NCCC1CCN(c2ccccc2)CC1

Participants

7

Reactant 2

HCID 11575IodobenzeneHCID 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 62657Potassium Phosphate, TribasicReagentHCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 2734558Bis(tri-tert-butylphosphine)palladium(0)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of tert-butyl 2-(piperidin-4-yl)ethylcarbamate (0.342 g, 1.5 mmol) in anhydrous DME were added iodobenzene (0.444 g, 2.18 mmol), bis(tri-t- butylphosphine)palladium(0) (0.077 g, 0.15 mmol) and potassium phosphate (0.245 mL, 3.00 mmol). The reaction was heated to 100°C overnight. This reaction did not work.

Sources & evidence

ORD record
ord-cc832050b1854993a53bbd02bde64312
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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