N,N,N',N'-Tetramethylmethanediamine → HCID 19042884, compound

HRID 1683290Notes

Reaction equation

HRID 1683290 reaction equation
CN(CN(C)C)C.C(Cl)(=O)C.[Cl:12][C:13]1[C:21]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[CH:16][NH:17]2.C[N:30]([CH2:32][C:33]1C2C(=CC=C(OC3C=CC=CC=3)C=2Cl)NC=1)C.[C-]#N.[K+].CI>C(Cl)Cl.CN(C=O)C.CCCCCC.CCOCC>[C:32]([CH2:33][C:15]1[C:14]2[C:18](=[CH:19][CH:20]=[C:21]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:13]=2[Cl:12])[NH:17][CH:16]=1)#[N:30]

Participants

10

Reactant 6

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 6328Methyl iodideHCID 6367Acetyl chlorideHCID 9032Potassium CyanideHCID 19042843HCID 19042843, compoundHCID 19042883HCID 19042883, compound

Product 1

HCID 19042884HCID 19042884, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 21584099Diethylether hexaneSolvent

Procedure

Treatment of a cooled solution of N,N,N',N'-tetramethyldiaminomethane (0.083 g, 0.11 mL, 0.812 mmol) in CH2Cl2 (2.4 mL) with acetyl chloride (0.064 g, 0.057 mL, 0.80 mmol) followed by a solution of 4-chloro-5-phenoxy indole (0.14 g, 0.574 mmol) in CH2Cl2 (2 mL), gave after work-up: 3-(N,N-dimethylaminomethyl)4-chloro-5-phenoxyindole, as an off-white solid. This was treated with potassium cyanide (0.143 g, 2.19 mmol) and methyl iodide (0.0.33 g, 0.143 mL, 2.29 mmol) in DMF (1 mL) for 16 hr After appropriate work-up and chromatography (silica gel; hexane/Et2O; 0-55%), 3-cyanomethyl-4-chloro-5-phenoxyindole was obtained as an off-white crystalline solid, 0.094 g (58%).

Workup

  1. customgave after work-up

Sources & evidence

ORD record
ord-7e8be01d48544527952147464380b887
Source dataset
uspto-grants-1997_06
Patent number
US05637593

Reaction notes

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