Sodium Bicarbonate → HCID 22141125, compound

HRID 1826437Notes

Reaction equation

HRID 1826437 reaction equation
[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([C:14]2[CH:15]=[C:16]([NH:20][C:21](=[O:23])[CH3:22])[CH:17]=[CH:18][CH:19]=2)[CH3:13])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].F[B-](F)(F)F.[O:29]=[N+:30]=[O:31].C(=O)([O-])O.[Na+]>C(#N)C>[CH2:1]([N:7]1[CH2:8][CH:9]2[CH:11]([C:10]2([C:14]2[CH:19]=[CH:18][C:17]([N+:30]([O-:31])=[O:29])=[C:16]([NH:20][C:21](=[O:23])[CH3:22])[CH:15]=2)[CH3:13])[CH2:12]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 11073463Nitronium tetrafluoroborateHCID 22141181HCID 22141181, compound

Product 1

HCID 22141125HCID 22141125, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-[3-(3-hexyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl]acetamide (Preparation 45, 1.5 g, 4.78 mmol) in acetonitrile (20 ml) at 0° C. was added nitronium tetrafluoroborate (1.0 g, 7.53 mmol) in several portions over 5 minutes. The mixture was stirred at 0° C. for 30 minutes and then saturated sodium hydrogen carbonate solution (30 ml) was added. The aqueous mixture was extracted with ethyl acetate (3×15 ml) and the combined extracts were dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by silica column chromatography eluting with ethyl acetate:hexane (50:50) to afford the title compound (534 mg, 32%) as pale yellow platelets.

Workup

  1. extractionThe aqueous mixture was extracted with ethyl acetate (3×15 ml)
  2. dry with materialthe combined extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by silica column chromatography
  6. washeluting with ethyl acetate:hexane (50:50)

Sources & evidence

ORD record
ord-fd17c051d9c34596869e6fe4733366ed
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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