Sodium Cyanide → HCID 22882817, compound

HRID 863538Notes

Reaction equation

HRID 863538 reaction equation
[C-:1]#[N:2].[Na+].CS(O[CH2:9][C@H:10]1[CH2:22][CH2:21][N:13]2[C:14]3[C:19]([CH:20]=[C:12]2[CH2:11]1)=[CH:18][CH:17]=[CH:16][CH:15]=3)(=O)=O>CN(C)C=O.C(OCC)(=O)C>[CH:18]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:19]=1[CH:20]=[C:12]1[CH2:11][C@@H:10]([CH2:9][C:1]#[N:2])[CH2:22][CH2:21][N:13]12

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 22882816HCID 22882816, compound

Product 1

HCID 22882817HCID 22882817, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

18.0 g (367 mmol) of sodium cyanide were added to a solution of 65.0 g (233 mmol) of (6,7,8,9-tetrahydropyrido[1,2-a]indol-8(S)-yl)methyl methanesulfonate in 500 ml of dimethylformamide and the mixture was heated at 70° C. for 24 hours. The mixture was partitioned between 1000 ml of water and 600 ml of ethyl acetate. The aqueous phase was extracted twice with 700 ml of ethyl acetate each time and the combined extracts were washed in twice with 500 ml of water each time, dried over magnesium sulfate and evaporated. The brown solid obtained was dissolved in ethyl acetate and the solution was filtered through a pad of silica gel. The solvent was removed in a vacuum and the residue was crystallized from methanol to give 25.8 g of 6,7,8,9-tetrahydropyrido[1,2-a]indole-8(S)-acetonitrile as a light brown solid of melting point 100°-101° C.; [α]D20 -40.6° (c=0.84%, CH2Cl2).

Workup

  1. customThe mixture was partitioned between 1000 ml of water and 600 ml of ethyl acetate
  2. extractionThe aqueous phase was extracted twice with 700 ml of ethyl acetate each time
  3. washthe combined extracts were washed in twice with 500 ml of water each time
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe brown solid obtained
  7. filtrationthe solution was filtered through a pad of silica gel
  8. customThe solvent was removed in a vacuum
  9. customthe residue was crystallized from methanol

Sources & evidence

ORD record
ord-c331811c56d54f10beb2b7212a3c8980
Source dataset
uspto-grants-1998_02
Patent number
US05721230

Reaction notes

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