Isopropanol → HCID 67149027, compound

HRID 494373Notes

Reaction equation

HRID 494373 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7]([CH2:9][C:10]([O:12][CH3:13])=[O:11])#[N:8].[C:14](=[O:17])([O-])[O-:15].[K+].[K+].[C-]#N.[K+].[CH:23](O)(C)[CH3:24]>>[C:6]([CH:5]([C:4]1([C:14]([O:15][CH2:23][CH3:24])=[O:17])[CH2:2][CH2:3]1)[CH:9]([C:7]#[N:8])[C:10]([O:12][CH3:13])=[O:11])#[N:1]

Participants

6

Reactant 5

HCID 3776IsopropanolHCID 7747Methyl cyanoacetateHCID 8082PiperidineHCID 9032Potassium CyanideHCID 11430Potassium Carbonate

Product 1

HCID 67149027HCID 67149027, compound

Procedure

To a mixture of Preparation 221 (9.35 g, 65.80 mmol), piperidine (0.65 ml, 6.58 mmol), methyl cyanoacetate (5.80 ml, 65.80 mmol) and potassium carbonate (0.91 g, 6.58 mmol) in isopropyl alcohol (120 ml) was added potassium cyanide (4.30 g, 65.80 mmol). The reaction mixture was stirred at room temperature for 18 h and then concentrated in vacuo. The residue was partitioned between hydrochloric acid (1M) and ethyl acetate and the two layers were separated. The aqueous layer was extracted with ethyl acetate and the combined extracts were washed with brine, dried (MgSO4) and concentrated in vacuo.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between hydrochloric acid (1M) and ethyl acetate
  3. customthe two layers were separated
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washthe combined extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-443c5363b0154f83ac125be924bfffe8
Source dataset
uspto-grants-2009_05
Patent number
US07538134B2

Reaction notes

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