N,N,N',N'-Tetramethylmethanediamine → 3-Cyanomethyl-5-phenoxyindole

HRID 1683280

Reaction equation

HRID 1683280 reaction equation
CN(C[N:5]([CH3:7])C)C.[O:8]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[CH:18]2)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+].Cl[CH2:27]Cl>C(Cl)(=O)C.[Cl-].[Na+].O>[C:7]([CH2:27][C:18]1[C:17]2[C:21](=[CH:22][CH:23]=[C:15]([O:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:16]=2)[NH:20][CH:19]=1)#[N:5]

Participants

7

Reactant 4

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 112412535-phenoxy-1H-indole

Product 1

HCID 190428863-Cyanomethyl-5-phenoxyindole

Reagents, catalysts & solvents 2

HCID 6367Acetyl chlorideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a cooled (ice bath) solution of bis (dimethylamino)methane (0.34 g) in dichloromethane (25 ml), acetyl chloride was added dropwise over 5 minutes. After stirring for 10 minutes, 5-phenoxyindole (0.51 g) was added and stirring continued for a further one hour at room temperature. The mixture was basified with aqueous 2N sodium hydroxide, brine (50 ml) added and the organic phase separated washed with water (2×50 ml), dried (MgSO4) and the solvent removed at reduced pressure. The residue was dissolved in dimethylformamide (25 ml) and potassium cyanide (0.62 g) and iodomethane (0.61 g) added. After stirring for 48 hours, the mixture was diluted with water (50 ml) and extracted with ethyl acetate (3×50 ml). The combined organic phases were washed with water (4×50 ml), dried (MgSO4) and solvent removed at reduced pressure to give 3-cyanomethyl-5-phenoxyindole (0.57 g).

Workup

  1. additionwas added dropwise over 5 minutes
  2. stirringstirring
  3. waitcontinued for a further one hour at room temperature
  4. additionadded
  5. customthe organic phase separated
  6. washwashed with water (2×50 ml)
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed at reduced pressure
  9. dissolutionThe residue was dissolved in dimethylformamide (25 ml)
  10. additionpotassium cyanide (0.62 g) and iodomethane (0.61 g) added
  11. stirringAfter stirring for 48 hours
  12. additionthe mixture was diluted with water (50 ml)
  13. extractionextracted with ethyl acetate (3×50 ml)
  14. washThe combined organic phases were washed with water (4×50 ml)
  15. dry with materialdried (MgSO4) and solvent
  16. customremoved at reduced pressure

Sources & evidence

ORD record
ord-57d367acd9094def968ed276d7b6163b
Source dataset
uspto-grants-1997_06
Patent number
US05637593

Linked notes

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