N,N,N',N'-Tetramethylmethanediamine → HCID 19042901, compound

HRID 1683287Notes

Reaction equation

HRID 1683287 reaction equation
CN(CN(C)C)C.C(Cl)(=O)C.[F:12][C:13]([F:31])([F:30])[C:14]1[CH:15]=[C:16]([CH:27]=[CH:28][CH:29]=1)[O:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[CH:21]2.C[N:33]([CH2:35][C:36]1C2C(=CC=C(OC3C=CC=C(C(F)(F)F)C=3)C=2)NC=1)C.[C-]#N.[K+].CI>C(Cl)Cl.CN(C=O)C>[C:35]([CH2:36][C:21]1[C:20]2[C:24](=[CH:25][CH:26]=[C:18]([O:17][C:16]3[CH:27]=[CH:28][CH:29]=[C:14]([C:13]([F:12])([F:30])[F:31])[CH:15]=3)[CH:19]=2)[NH:23][CH:22]=1)#[N:33]

Participants

9

Reactant 6

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 6328Methyl iodideHCID 6367Acetyl chlorideHCID 9032Potassium CyanideHCID 19042861HCID 19042861, compoundHCID 19042895HCID 19042895, compound

Product 1

HCID 19042901HCID 19042901, compoundYield 0%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

Treatment of a cooled solution of N,N,N',N'-tetramethyldiaminomethane (0.26 g, 0.34 mL, 2.50 mmol) in CH2Cl2 (7.3 mL) with acetyl chloride (0.20 g, 0.18 mL, 2.53 mmol) followed by a solution of 5-(3-trifluoromethylphenoxy) indole (0.50 g, 1.79 mmol) in CH2Cl2 (6.2 mL), gave after work-up: 3-(N,N-dimethylaminomethyl)-5-(3-trifluoromethylphenoxy)indole as a gum. This was treated with finely ground potassium cyanide (0.45 g, 6.9 mmol) and methyl iodide (1.03 g, 0.45 mL, 7.26 mmol) in DMF (9 mL) for 16 hr, and after appropriate work-up and chromatography (silica gel; hexane/Et2O; 0-45%) 3-cyanomethyl-5-(3-trifluoromethylphenoxy)indole was obtained as an almost colourless gum, 0.415 g (73%).

Workup

  1. customgave after work-up

Sources & evidence

ORD record
ord-455c06e59b9e4a8fb28c369527e48d8e
Source dataset
uspto-grants-1997_06
Patent number
US05637593

Reaction notes

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