Potassium Cyanide → HCID 67337158, compound

HRID 1921216Notes

Reaction equation

HRID 1921216 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]2[C:3]=1[C:4]([CH2:12]N(C)C)=[CH:5][NH:6]2.[C-:16]#[N:17].[K+]>CN(C=O)C.O>[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]2[C:3]=1[C:4]([CH2:12][C:16]#[N:17])=[CH:5][NH:6]2

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 67336549HCID 67336549, compound

Product 1

HCID 67337158HCID 67337158, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of [(4,6-dimethyl-1H-indol-3-yl)methyl]dimethylamine from Step A (98.0 mg, 0.484 mmol) and potassium cyanide (315 mg, 4.84 mmol) in DMF (2 mL) and H2O (2 mL) was heated at 100° C. for 2 h. The reaction mixture was partitioned between EtOAc (20 mL) and saturated NaCl (10 mL). The layers were separated and the organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the crude product by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH—100:0 to 98:2, gave the title compound. MS: m/z=185 (M+1).

Workup

  1. customThe reaction mixture was partitioned between EtOAc (20 mL) and saturated NaCl (10 mL)
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the crude product by silica gel chromatography
  7. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-23cc9d081da94aa1b9008e2f2fe4ad43
Source dataset
uspto-grants-2012_05
Patent number
US08173655B2

Reaction notes

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