Water → HCID 44252387, compound

HRID 76924Notes

Reaction equation

HRID 76924 reaction equation
[CH2:1]([C:8]1([CH2:19][N:20]([CH3:22])[CH3:21])[CH2:13][CH2:12][C:11]([N:16]([CH3:18])[CH3:17])([C:14]#N)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1([Mg]Cl)[CH:28]=[CH:27]C=[CH:25][CH:24]=1.[NH4+].[Cl-].O>C1COCC1>[CH2:1]([C:8]1([CH2:19][N:20]([CH3:21])[CH3:22])[CH2:13][CH2:12][C:11]([N:16]([CH3:17])[CH3:18])([C:14]2[CH:27]=[CH:28][CH:23]=[CH:24][CH:25]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 686314524-Benzyl-1-(dimethylamino)-4-((dimethylamino)methyl)cyclohexane carbonitrileHCID 178478979HCID 178478979, compound

Product 1

HCID 44252387HCID 44252387, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound of step 1 (0.88 g, 2.94 mmol) was dissolved in THF (35 mL) and mixed in drops with 2M phenylmagnesium chloride solution (5.1 mL, 10.2 mmol) with ice cooling. The reaction solution was heated to boiling for 8 h. For work up the solution was mixed with 20% NH4Cl solution (0.6 mL) and water (0.4 mL) with ice cooling, extracted with ether (3×25 mL), the ether solution was washed with water, dried (Na2SO4) and concentrated to low volume in a vacuum. The residue was purified by column chromatography with EtOH/EE (1:20). 2 fractions were obtained, wherein according to LCMS, inter alia, the more polar fraction (300 mg) contained the desired substance.

Workup

  1. temperatureThe reaction solution was heated
  2. extractionextracted with ether (3×25 mL)
  3. washthe ether solution was washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to low volume in a vacuum
  6. customThe residue was purified by column chromatography with EtOH/EE (1:20)
  7. custom2 fractions were obtained

Sources & evidence

ORD record
ord-d90be85c97b64aca98b76ff78f3f5df4
Source dataset
uspto-grants-2014_09
Patent number
US08835689B2

Reaction notes

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