N,N,N',N'-Tetramethylmethanediamine → 3-Dimethylaminomethyl-4-chloro-5-n-propyloxyindole

HRID 1898989Notes

Reaction equation

HRID 1898989 reaction equation
[Cl:1][C:2]1[C:10]([O:11][CH2:12][CH2:13][CH3:14])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[CH3:15][N:16]([CH2:18]N(C)C)[CH3:17].C(Cl)(=O)C>ClCCl>[CH3:15][N:16]([CH2:18][C:4]1[C:3]2[C:7](=[CH:8][CH:9]=[C:10]([O:11][CH2:12][CH2:13][CH3:14])[C:2]=2[Cl:1])[NH:6][CH:5]=1)[CH3:17]

Participants

5

Reactant 3

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 6367Acetyl chlorideHCID 233730884-Chloro-5-n-propyloxyindole

Product 1

HCID 233731103-Dimethylaminomethyl-4-chloro-5-n-propyloxyindoleYield 78.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treatment of 4-chloro-5-n-propyloxyindole (5.10 g, 24.3 mmol) with bis (dimethylamino)methane (BDAM) (3.34 g, 32.7 mmol) and acetyl chloride (2.57 g, 32.7 mmol) in dichloromethane by the method described in 1 (c) gave 3-dimethylaminomethyl-4-chloro-5-n-propyloxyindole (5.11 g) as a sticky solid.

Sources & evidence

ORD record
ord-7f7b6ee034b94e49b06ef68e81b0b824
Source dataset
uspto-grants-1996_11
Patent number
US05571833

Reaction notes

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