Water → HCID 22038338, compound

HRID 1790527Notes

Reaction equation

HRID 1790527 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([CH:23]=[O:24])[CH:21]=4)[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:27][Mg]Br.[Cl-].[NH4+].[OH2:32].[C:33]([O:36]CC)(=[O:35])[CH3:34]>O1CCCC1.CCOCC>[C:33]([OH:36])(=[O:35])[C:34]([OH:24])=[O:32].[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH:11]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([CH:23]([OH:24])[CH3:27])[CH:21]=4)[CH:16]=[CH:15]3)[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 962WaterHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 220380721-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-formylindolineHCID 178418573HCID 178418573, compound

Product 1

HCID 22038338HCID 22038338, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-formylindoline (0.15 g) obtained in Example 130 was dissolved in tetrahydrofuran (5 ml) and stirred under ice cooling. To the resultant solution was added a 1.0 M solution (0.5 ml) of methylmagnesium bromide in ether and the mixture was stirred for 30 min. Then a saturated aqueous solution of ammonium chloride, water and ethyl acetate were added to the reaction solution. The organic layer was separated, washed successively with water and brine and dried over magnesium sulfate. After evaporating the solvent under reduced pressure, a free title compound (0.13 g) was obtained as a pale brown viscous oil, which was then converted into an oxalate in a conventional manner.

Workup

  1. stirringthe mixture was stirred for 30 min
  2. customThe organic layer was separated
  3. washwashed successively with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporating the solvent under reduced pressure

Sources & evidence

ORD record
ord-5af42bbbaf3f46088edb01a641e798f2
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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