Dimethylamine → 1-(5-Chloro-1H-indol-3-yl)-N,N-dimethylmethanamine

HRID 1719386Notes

Reaction equation

HRID 1719386 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH3:11][NH:12][CH3:13].[CH2:14]=O>C(O)(=O)C>[CH3:11][N:12]([CH2:14][C:5]1[C:4]2[CH:3]=[C:2]([Cl:1])[CH:10]=[CH:9][C:8]=2[NH:7][CH:6]=1)[CH3:13]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 871105-Chloroindole

Product 1

HCID 134914391-(5-Chloro-1H-indol-3-yl)-N,N-dimethylmethanamine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The starting material is prepared as follows: 5-Chloroindole (4.00 g) is added to a mixture of 40% aqueous dimethylamine (4.5 ml), and 37% aqueous formaldehyde (2.6 ml) in glacial acetic acid (6.4 ml) while stirring at 10°. The cooling bath is removed and the mixture stirred at room temperature for 3 hours. The mixture is made basic with ammonium hydroxide whereupon a precipitate is formed. The solid is collected, washed with water and dried to give 5-chloro gramine, m.p. 149°-151°.

Workup

  1. customThe starting material is prepared
  2. customThe cooling bath is removed
  3. stirringthe mixture stirred at room temperature for 3 hours
  4. customis formed
  5. customThe solid is collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-780c9d5129b74f7d88d6c824031d76ed
Source dataset
uspto-grants-1985_09
Patent number
US04539410

Reaction notes

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