N,N,N',N'-Tetramethylmethanediamine → HCID 19042913, compound

HRID 1683295Notes

Reaction equation

HRID 1683295 reaction equation
CN([CH2:4][N:5]([CH3:7])[CH3:6])C.C(Cl)(=O)C.[Br: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(Cl)Cl>[CH3:7][N:5]([CH2:4][C:22]1[NH:23][C:24]2[C:20]([CH:21]=1)=[CH:19][C:18]([O:17][C:16]1[CH:27]=[CH:28][C:13]([Br:12])=[CH:14][CH:15]=1)=[CH:26][CH:25]=2)[CH3:6]

Participants

5

Reactant 3

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 6367Acetyl chlorideHCID 190429125-(4-Bromophenoxy)-1H-indole

Product 1

HCID 19042913HCID 19042913, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Treatment of a cooled solution of N,N,N',N'-tetramethyldiaminomethane (0.186 g, 0.25 mL, 1.83 mmol) in CH2Cl2 (10 mL) with acetyl chloride (0.143 g, 0.13 mL, 1.83 mmol) followed by a solution of 5-(4-bromophenoxy)indole (0.394 g, 1.37 mmol) in CH2Cl2 (5 mL), gave after work-up 2-(N,N-dimethylaminomethyl)-5-(4-bromophenoxy)indole as a brown gum. This was treated with finely ground potassium cyanide (0.34 g, 5.21 mmol) and methyl iodide (0.77 g, 0.34 mL, 5.44 mmol) in DMF (30 mL) for 16 hr, and after appropriate work-up, 3-cyanomethyl-5-(4-bromophenoxy)indole was obtained as a brown gum 0.29 g, (ca 65%; carried through to next stage without further purification).

Sources & evidence

ORD record
ord-503ce70b61c746e59d7e483ae1727839
Source dataset
uspto-grants-1997_06
Patent number
US05637593

Reaction notes

Loading…