Water → HCID 21096958, compound

HRID 1663027Notes

Reaction equation

HRID 1663027 reaction equation
[C-:1]#[N:2].[K+].Cl[CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][N:14]=2)[CH2:9][CH2:8]1.[I-].[K+].O>CS(C)=O.C(OCC)(=O)C>[C:13]1([N:10]2[CH2:11][CH2:12][CH:7]([CH2:6][CH2:5][C:1]#[N:2])[CH2:8][CH2:9]2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][N:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 4875Potassium IodideHCID 9032Potassium CyanideHCID 21096913HCID 21096913, compound

Product 1

HCID 21096958HCID 21096958, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

0.63 g (9.57 mmol) of potassium cyanide is added portionwise to a suspension of 2.63 g (9.57 mmol) of 1-[4-(2-chloroethyl)-1-piperidyl]isoquinoline, prepared in step 2.2, and 0.048 g (0.29 mmol) of potassium iodide in 30 ml of dimethyl sulfoxide. The reaction mixture is maintained at about 120° C. for 16 hours. The mixture is allowed to cool to room temperature and 90 ml of water and ethyl acetate are then added. The aqueous phase is separated out and extracted three times with ethyl acetate, the combined organic phases are washed with saturated aqueous sodium chloride solution and dried over sodium sulfate, and the filtrate is concentrated under reduced pressure. The residue thus obtained is purified by chromatography on silica gel, eluting with a 30/70 mixture of ethyl acetate and cyclohexane.

Workup

  1. temperatureto cool to room temperature
  2. customThe aqueous phase is separated out
  3. extractionextracted three times with ethyl acetate
  4. washthe combined organic phases are washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customThe residue thus obtained
  8. customis purified by chromatography on silica gel
  9. washeluting with a 30/70 mixture of ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-1772bd5cd4e940acab2f02d2db83df6e
Source dataset
uspto-grants-2011_10
Patent number
US08034818B2

Reaction notes

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