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Iodobenzene → N-(2-(Dimethylamino)ethyl)aniline

HRID 135
Notes
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Reaction equation

HRID 135 reaction equation
CN(C)CCN.Ic1ccccc1>CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.CN(C)C=O.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd]>CN(C)CCNc1ccccc1
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 11575IodobenzeneHCID 66053N,N-Dimethylethylenediamine

Product 1

HCID 81206N-(2-(Dimethylamino)ethyl)anilineYield 0%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)Catalyst

Conditions

Temperature
100 °C

Procedure

In a 50 mL round-bottomed flask (t=g) was unsym-Dimethylethylenediamine (1.080 mL, 9.80 mmol), Iodobenzene (0.549 mL, 4.90 mmol), and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.449 g, 0.49 mmol)Cesium carbonate (2.396 g, 7.35 mmol) andCesium carbonate (2.396 g, 7.35 mmol) were added. in DMF (10 mL) ([VOLUME]) to give a brown suspension. Reaction stirred over night at 100°C. no reaction.

Sources & evidence

ORD record
ord-6eea29be7d4b47c5893b1e243ef41836
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes
HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 6228DimethylformamideSolvent