Methyl iodide → 3-Cyanomethyl-4-chloro-5-benzyloxyindole

HRID 1898985Notes

Reaction equation

HRID 1898985 reaction equation
[C-:1]#[N:2].[K+].CN([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:15]=2[Cl:17])[NH:10][CH:9]=1)C.CI.S([O-])([O-])(=O)=O.[Na+].[Na+]>CN(C=O)C>[C:1]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:15]=2[Cl:17])[NH:10][CH:9]=1)#[N:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 9032Potassium CyanideHCID 24436Sodium SulfateHCID 233730643-Dimethylaminomethyl-4-chloro-5-benzyloxy-indole

Product 1

HCID 233730833-Cyanomethyl-4-chloro-5-benzyloxyindoleYield 63.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium cyanide (7.36 g, 113 retool) was added to a solution of 3-dimethylaminomethyl-4-chloro-5-benzyloxy-indole (9.30 g, 29.5 mmol) in sieve-dried DMF (150 ml). Methyl iodide (17.2 g, 121 mmol) was added dropwise, while stirring over 15 minutes, and stirring was continued for a further hour. The mixture was poured into 10% aqueous sodium sulphate and extracted with diethyl ether. The combined extracts were dried (Na2SO4) and evaporated to dryness leaving an oil which crystallised. Recrystallisation from methanol gave 3-cyanomethyl-4-chloro-5-benzyloxyindole (5.56 g), m.p. 130°-2° C.

Workup

  1. stirringstirring
  2. waitwas continued for a further hour
  3. extractionextracted with diethyl ether
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. customevaporated to dryness
  6. customleaving an oil which
  7. customcrystallised
  8. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-61b3dab60b4c4cc49519606baade3ca7
Source dataset
uspto-grants-1996_11
Patent number
US05571833

Reaction notes

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