1-Bromo-2-methylpropane → HCID 22149716, compound

HRID 1824481Notes

Reaction equation

HRID 1824481 reaction equation
[Mg].[CH2:2](Br)[CH:3]([CH3:5])[CH3:4].[N:7]1([C:13]2[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=2[CH:15]=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>CCOCC>[CH3:4][CH:3]([CH3:5])[CH2:2][CH:15]([OH:16])[C:14]1[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=1[N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropane3×HCID 20621572-(Piperidin-1-yl)benzaldehydeHCID 5462224Magnesium

Product 1

HCID 22149716HCID 22149716, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

In a 3 necked round bottom flask (25 ml), equipped with a dropping funnel, reflux condenser and thermometer pocket, placed magnesium turnings (0.254 gm, 10.47 mmol) and flame dried the apparatus. Dry diethyl ether (10 ml.) was added to Mg. Turning, Isobutyl bromide (1.13 ml, 1.45 gm, 10.58 mmol) was taken in 2 ml of dry ether and added drop wise to the Mg turnings. As soon as ether starts boiling (in a few minutes) the reaction was cooled using ice-salt and continued the addition of isobutyl bromide. After complete addition of isobutyl bromide continued for another 20 minutes. o-piperidino benzaldehyde 8 (1.0 gm, 5.29 mmol) in 2 ml of ether was added drop wise at −10° C. After the completion of addition of 8 continued the stirring for 1 hr and the reaction was quenched with ice-cooled saturated ammonium chloride solution (5 ml), the solid separated is filtered off, the filtrate is extracted with ethyl acetate (10×2 ml) dried over sodium sulphate and concentrated to yield 1.36 gm of crude product. The crude product was chromatographed and obtained pure 9 (54.2%).

Workup

  1. customIn a 3 necked round bottom flask (25 ml), equipped with a dropping funnel
  2. temperaturereflux condenser
  3. temperatureflame
  4. customdried the apparatus
  5. additionDry diethyl ether (10 ml.) was added to Mg
  6. custom(in a few minutes)
  7. temperaturewas cooled
  8. additionAfter the completion of addition of 8
  9. customstirring for 1 hr
  10. customthe reaction was quenched with ice-
  11. temperaturecooled saturated ammonium chloride solution (5 ml)
  12. customthe solid separated
  13. filtrationis filtered off
  14. extractionthe filtrate is extracted with ethyl acetate (10×2 ml)
  15. dry with materialdried over sodium sulphate
  16. concentrationconcentrated
  17. customto yield 1.36 gm of crude product
  18. customThe crude product was chromatographed

Sources & evidence

ORD record
ord-966b988b0d2147d5acdd55f744194f77
Source dataset
uspto-grants-2006_05
Patent number
US07041830B2

Reaction notes

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