N,N,N',N'-Tetramethylmethanediamine → 3-Cyanomethyl-5-(4-methylphenoxy)indole

HRID 1683285Notes

Reaction equation

HRID 1683285 reaction equation
CN(CN(C)C)C.C(Cl)(=O)C.[CH3:12][C:13]1[CH:28]=[CH:27][C:16]([O:17][C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[NH:23][CH:22]=[CH:21]3)=[CH:15][CH:14]=1.C[N:30]([CH2:32][C:33]1C2C(=CC=C(OC3C=CC(C)=CC=3)C=2)NC=1)C.[C-]#N.[K+].CI>C(Cl)Cl.CN(C=O)C>[C:32]([CH2:33][C:21]1[C:20]2[C:24](=[CH:25][CH:26]=[C:18]([O:17][C:16]3[CH:27]=[CH:28][C:13]([CH3:12])=[CH:14][CH:15]=3)[CH:19]=2)[NH:23][CH:22]=1)#[N:30]

Participants

9

Reactant 6

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 6328Methyl iodideHCID 6367Acetyl chlorideHCID 9032Potassium CyanideHCID 190429083-(N,N-dimethylaminomethyl)-5-(4-methylphenoxy)indoleHCID 220488355-(4-methylphenoxy)-1H-indole

Product 1

HCID 190429233-Cyanomethyl-5-(4-methylphenoxy)indole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

Treatment of a cooled solution of N,N,N',N'-tetramethyldiaminomethane (0.24 g, 0.32 mL, 2.35 mmol) in CH2Cl2 (7 mL) with acetyl chloride (0.19 g, 0.17 mL, 2.39 mmol) followed by a solution of 5-(4-methylphenoxy)indole (0.39 g, 1.74 mmol) in CH2Cl2 (6 mL), gave after work-up: 3-(N,N-dimethylaminomethyl)-5-(4-methylphenoxy)indole as a gum. This was treated with potassium cyanide (0.43 g, 6.6 mmol) and methyl iodide (0.98 g, 0.43 mL, 6.9 mmol) in DMF (6 mL) for 16 hr, and after appropriate work-up, 3-cyanomethyl-5-(4-methylphenoxy)indole was obtained as an off-white crystalline solid 0.338 g (74%).

Workup

  1. customgave after work-up

Sources & evidence

ORD record
ord-53fc89776c3f443fb0eb8143c724ac33
Source dataset
uspto-grants-1997_06
Patent number
US05637593

Reaction notes

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