Sodium Cyanide → HCID 58999618, compound

HRID 1593622Notes

Reaction equation

HRID 1593622 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH:7]([CH2:15]OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:6][C:5]2=1.[C-:27]#[N:28].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH:7]([CH2:15][C:27]#[N:28])[CH2:6][C:5]2=1

Participants

4

Reactant 2

HCID 8929Sodium Cyanide2×HCID 58999615HCID 58999615, compound

Product 1

HCID 58999618HCID 58999618, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of the crude toluene-4-sulfonic acid 6-fluoro-2,3,4,9-tetrahydro-1H-carbazol-3-yl-methyl ester (9.827 g, 0.0263 mol) in ethanol (70 mL) was added solid sodium cyanide (49.01 g, 0.0447 mol). The mixture was stirred at gentle reflux for 16 hours. Following TLC, a small amount of additional sodium cyanide was added and heating resumed for 2 hours. Most of the solvent was removed under reduced pressure (ca 55 mL). The residue was slurried in water (70 mL) and extracted with diethyl ether (3×). The extracts were washed with water and brine, and dried over anhydrous magnesium sulfate. Removal of the solvent provided a mustard colored solid which was purified by flash chromatography on silica gel Merck-60 using a gradient from 8:2 to 1:1 of ethyl acetate in hexane. The desired title compound was obtained as a yellow oil that solidifies in vacuo to yield light yellow crystals (5.2 g), m.p. 136-138° C. MS (ES): [M−H]− @m/z 227.1.

Workup

  1. temperatureat gentle reflux for 16 hours
  2. temperatureheating
  3. customMost of the solvent was removed under reduced pressure (ca 55 mL)
  4. extractionextracted with diethyl ether (3×)
  5. washThe extracts were washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customRemoval of the solvent
  8. customprovided a mustard colored solid which
  9. customwas purified by flash chromatography on silica gel Merck-60

Sources & evidence

ORD record
ord-7af35defc73c49019d060d65f3f832c6
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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