Benzyl Bromide → HCID 10469057, compound

HRID 1111109Notes

Reaction equation

HRID 1111109 reaction equation
[OH:1][C:2]1([C:8]2[CH:9]=[CH:10][C:11]([O:14]C)=[N:12][CH:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:1][C:2]1([C:8]2[CH:9]=[CH:10][C:11](=[O:14])[N:12]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:13]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 10352983HCID 10352983, compound

Product 1

HCID 10469057HCID 10469057, compoundYield 109.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-(1-hydroxycyclohexyl)-2methoxy pyridine (26.3 g), benzyl bromide (21.7 g) and potassium carbonate (35 g) was heated in 500 mL of refluxing acetonitrile for 17 hours. The mixture was cooled and filtered, and the solids were washed with methanol. The filtrate was concentrated to give 39.5 g of an oil. HPLC on silica gel (elution with ethyl acetate) afforded 20.8 g of solid.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washthe solids were washed with methanol
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-6e030546c9cc40bd9d0f34b9e98bc5a0
Source dataset
uspto-grants-1990_12
Patent number
US04978663

Reaction notes

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