Hydrochloric Acid → [5-(2-methoxy-ethoxy)-1H-indol-ylmethyl]-dimethyl-amine

HRID 41060

Reaction equation

HRID 41060 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[CH:9]2.[CH2:15]=O.Cl.[CH3:18][NH:19][CH3:20]>C(O)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:18][N:19]([CH3:15])[CH3:20])[CH:10]=[CH:9]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 712FormaldehydeHCID 103525375-(2-methoxyethoxy)-1H-indole

Product 1

HCID 66938466[5-(2-methoxy-ethoxy)-1H-indol-ylmethyl]-dimethyl-amineYield 90%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 5-(2-methoxy-ethoxy)-indole (2.06 g, 11.0 mmol) in acetic acid (7 ml) and 40% aqueous dimethylamine (2.1 ml) is cooled to 0° C., and 36% aqueous formaldehyde (1.38 ml) (pre-cooled to 0° C.) is added drop wise. The mixture is stirred at room temperature overnight, 2 M hydrochloric acid is added, and the mixture is washed with dichloromethane. The aqueous layer is made alkaline with 10% NaOH, and is extracted with dichloromethane. The combined organic layer is washed with water, is dried and concentrated. The residue is purified by column chromatography (dichloromethane-methanol, 4:1→dichloromethane-methanol-water-aqueous ammonia, 10:20:1:1) to afford [5-(2-methoxy-ethoxy)-1H-indol-ylmethyl]-dimethyl-amine (2.42 g, 90%). M.p. 163-164° C. (from toluene-N,N-dimethylformamide).

Workup

  1. washthe mixture is washed with dichloromethane
  2. extractionis extracted with dichloromethane
  3. washThe combined organic layer is washed with water
  4. customis dried
  5. concentrationconcentrated
  6. customThe residue is purified by column chromatography (dichloromethane-methanol, 4:1→dichloromethane-methanol-water-aqueous ammonia, 10:20:1:1)

Sources & evidence

ORD record
ord-647412664e524dd98d16f3f196ff2ed6
Source dataset
uspto-grants-2013_09
Patent number
US08530493B2

Linked notes

Loading…