Carbon tetrabromide → 2-[4-(3-Bromoprop-2-ynylidene)piperidin-1-yl]-3-nitropyridine

HRID 1896020Notes

Reaction equation

HRID 1896020 reaction equation
[N+:1]([C:4]1[C:5]([N:10]2[CH2:15][CH2:14][C:13](=[CH:16][C:17]#[CH:18])[CH2:12][CH2:11]2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(Br)(Br)(Br)[Br:20].[OH-].[K+]>C1C=CC=CC=1>[Br:20][C:18]#[C:17][CH:16]=[C:13]1[CH2:14][CH2:15][N:10]([C:5]2[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[CH:7][N:6]=2)[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 14797Potassium HydroxideHCID 866273353-Nitro-2-(4-prop-2-ynylidenepiperidin-1-yl)pyridine

Product 1

HCID 867620142-[4-(3-Bromoprop-2-ynylidene)piperidin-1-yl]-3-nitropyridine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of Compound 1c (200 mg, 0.82 mmol), CBr4 (0.54 mg, 1.65 mmol), potassium hydroxide (0.138 mg, 2.46 mmol), 18-C-6 crown ether (21.8 mg, 0.823 mmol) and 10 mL of benzene was stirred at 65° C. for 11 h.

Sources & evidence

ORD record
ord-8ab1c961ce344584997291f1b9911867
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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