N,N,N',N'-Tetramethylmethanediamine → HCID 19042918, compound

HRID 1683292Notes

Reaction equation

HRID 1683292 reaction equation
CN(CN(C)C)C.C(Cl)(=O)C.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[NH:24][CH:23]=[CH:22]3)[CH:13]=1.C[N:29]([CH2:31][C:32]1C2C(=CC=C(OC3C=NC=CC=3)C=2)NC=1)C.[C-]#N.[K+].CI>C(Cl)Cl.CN(C=O)C.CCCCCC.CCOC(C)=O>[C:31]([CH2:32][C:22]1[C:21]2[C:25](=[CH:26][CH:27]=[C:19]([O:18][C:14]3[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=3)[CH:20]=2)[NH:24][CH:23]=1)#[N:29]

Participants

10

Reactant 6

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 6328Methyl iodideHCID 6367Acetyl chlorideHCID 9032Potassium CyanideHCID 19042860HCID 19042860, compoundHCID 19042919HCID 19042919, compound

Product 1

HCID 19042918HCID 19042918, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Treatment of a cooled solution of N,N,N',N'-tetramethyldiaminomethane (0.829 g, 1.11 mL, 8.12 mmol) in CH2Cl2 (10 mL) with acetyl chloride (0.637 g, 0.573 mL, 8.12 mmol) followed by a solution of 5-(pyrid-3-yloxy)indole (1.23 g, 5.8 mmol) in CH2Cl2 (100 mL), gave after work-up: 3-(N,N-dimethylaminomethyl)-5-(pyrid-3-yloxy)indole as a gum. This was treated with finely ground potassium cyanide (1.246 g, 19 mmol) and methyl iodide (2.7 g, 1.18 mL, 19 mmol) in DMF (70 mL) for 16 hr, and after appropriate work-up and chromatography (silica gel; hexane/EtOAc; 0-60%), 3-cyanomethyl-5-(pyrid-3-yloxy)indole was obtained a gum, which solidified on standing, 0.655 g (45%).

Workup

  1. customgave after work-up

Sources & evidence

ORD record
ord-b499a04a22c24e508d7265688416c43f
Source dataset
uspto-grants-1997_06
Patent number
US05637593

Reaction notes

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