HCID 57964165, compound → HCID 57964581, compound

HRID 2403530Notes

Reaction equation

HRID 2403530 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][N:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:20]=[C:21]([CH:28]=[CH:29][CH:30]=4)[C:22](N(OC)C)=[O:23])[CH2:15][CH2:14]3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH2:31]([Mg]Br)[CH3:32]>O1CCCC1.C(=O)([O-])O.[Na+]>[O:4]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][N:16]([C:19]4[CH:20]=[C:21]([C:22](=[O:23])[CH2:31][CH3:32])[CH:28]=[CH:29][CH:30]=4)[CH2:17][CH2:18]3)[CH2:7][CH2:6]2)[O:1][CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 57964165HCID 57964165, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 57964581HCID 57964581, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 1.6 g (3.8 mmol) of 3-{4-[2-(1,4-dioxaspiro[4.5]dec-8-yl)ethyl]piperazin-1-yl}-N-methoxy-N-methylbenzamide in 25 mL of dry tetrahydrofuran cooled to 0° C. are added 8 mL of 1M ethylmagnesium bromide solution in tetrahydrofuran. The mixture is stirred for 90 minutes then poured in 100 mL of an aqueous saturated sodium hydrogen carbonate solution. The product is extracted twice with ethyl acetate. The organic phases are combined, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue (1.4 g) is purified over 50 g of silica gel (eluant heptane/ethyl acetate 1/1) to give 1.06 g (72%) of 1-(3-{4-[2-(1,4-dioxaspiro[4.5]dec-8-yl)ethyl]piperazin-1-yl}phenyl)propan-1-one as an oil.

Workup

  1. extractionThe product is extracted twice with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue (1.4 g) is purified over 50 g of silica gel (eluant heptane/ethyl acetate 1/1)

Sources & evidence

ORD record
ord-42daf454f88d4adfb209fc87e4da7db0
Source dataset
uspto-grants-2014_08
Patent number
US08802678B2

Reaction notes

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