Hydrochloric Acid → HCID 23090950, compound

HRID 1820010Notes

Reaction equation

HRID 1820010 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CON(C)[C:12](=[O:29])[CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH3:23])=[CH:18][CH:17]=1.O.[ClH:32]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[ClH:32].[C:1]1([C:12](=[O:29])[CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]([N:24]3[CH2:25][CH2:26][CH2:27][CH2:28]3)[CH3:23])=[CH:18][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 23090958HCID 23090958, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 23090950HCID 23090950, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of phenylmagnesium bromide (2 mol/l THF solution, 1.6 ml) in toluene (7 ml) was added dropwise a solution of N-methoxy-N-methyl-4-{4-[1-(1-pyrrolidinyl)ethyl]phenyl}butanamide (200 mg, 0.66 mmol) obtained in Reference Example 89 in toluene (3 ml) under a nitrogen atmosphere under ice-cooling. After stirring at room temperature for 1 hr, the reaction solution was poured into water (40 ml), and extracted with ethyl acetate (40 ml×2). The extract was washed successively with 10% sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by NH-silica gel column chromatography (developing solvent; hexane:ethyl acetate=10:1) to give a colorless oil. The oil was dissolved in ethyl acetate (10 ml), and 4N-hydrochloric acid (ethyl acetate solution; 0.2 ml) was added dropwise under ice-cooling. The mixture was stirred for 5 min., and the solvent was evaporated under reduced pressure. The residue was powderized with isopropyl ether and hexane, and washed with hexane to give the title compound.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate (40 ml×2)
  3. washThe extract was washed successively with 10% sodium hydrogencarbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by NH-silica gel column chromatography (developing solvent; hexane:ethyl acetate=10:1)
  7. customto give a colorless oil
  8. temperaturecooling
  9. stirringThe mixture was stirred for 5 min.
  10. customthe solvent was evaporated under reduced pressure
  11. washwashed with hexane

Sources & evidence

ORD record
ord-e5b71e6ac2294ce7b12bf7baf55c2862
Source dataset
uspto-grants-2009_10
Patent number
US07601868B2

Reaction notes

Loading…