Toluene → Ammonia

HRID 1180498Notes

Reaction equation

HRID 1180498 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].CC(C)([O-])C.[K+].C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[NH3:4].[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([N:18]2[CH2:17][CH2:16][N:15]([C:13]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:14])[CH2:20][CH2:19]2)[CH:3]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 122863-BromopyridineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 2

HCID 222AmmoniaHCID 11673373Tert-butyl 4-(pyridin-3-YL)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-bromopyridine (7.8 g, 49.4 mmol), 1-ter-butoxycarbonylpiperazine (9.2 g, 49.4 mmol), tetrakis(triphenylphosphine)palladium(0) (286 mg, 0.247 mmol), potassium tert-butoxide (11.1 g, 98.8 mmol) and anhydrous toluene (100 ml) was stirred at 80° C. for 0.5 hours. Water (100 ml) was added and the mixture was extracted three times with ethyl acetate (75 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound as an oil. Yield 1.34 g, 10%.

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate (75 ml)

Sources & evidence

ORD record
ord-574b57bbb1b7417c9c302a4b7f44d020
Source dataset
uspto-grants-2007_10
Patent number
US07282494B2

Reaction notes

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