Diethylamine → HCID 18924852, compound

HRID 1288822Notes

Reaction equation

HRID 1288822 reaction equation
Cl[CH2:2][C:3]1[N:8]=[C:7]2[S:9][C:10]([CH3:13])=[C:11]([CH3:12])[C:6]2=[C:5]([C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)[C:4]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24].[CH2:28]([NH:30][CH2:31][CH3:32])[CH3:29]>ClCCl>[CH2:28]([N:30]([CH2:2][C:3]1[N:8]=[C:7]2[S:9][C:10]([CH3:13])=[C:11]([CH3:12])[C:6]2=[C:5]([C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)[C:4]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:31][CH3:32])[CH3:29]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 18924857HCID 18924857, compound

Product 1

HCID 18924852HCID 18924852, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 6-chloromethyl-4-(3,4-methylenedioxyphenyl)-2,3-dimethylthieno[2,3-b]pyridine-5-carboxylate (1.5 g), diethylamine (1.36 g) and dichloromethane (35 ml) was stirred for 14 hours under reflux. The reaction mixture was washed with water and dried (MgSO4), then the solvent was distilled off. The residue was subjected to column chromatography on silica gel. From the fraction eluted with chloroform, was obtained ethyl 6-(N,N-diethylaminomethyl)-4-(3,4-methylenedioxyphenyl)-2,3-dimethylthieno[2,3-b]pyridine-5-carboxylate as an oily product. This oily product was dissolved in ethanol (35 ml), to which was added ethanolic hydrogen chloride (23%, 1.2 g). The mixture was stirred for 15 minutes at room temperature, which was concentrated under reduced pressure to leave hydrochloride of ethyl 6-(N,N-diethylaminomethyl)-4-(3,4-methylenedioxyphenyl)-2,3-dimethylthieno[2,3-b]pyridine-5-carboxylate (0.8 g, 44%) as an amorphous solid product.

Workup

  1. temperatureunder reflux
  2. washThe reaction mixture was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationthe solvent was distilled off
  5. washFrom the fraction eluted with chloroform

Sources & evidence

ORD record
ord-dd50a98a0b0b4a34a5c91b0345a6d9a3
Source dataset
uspto-grants-1998_05
Patent number
US05747486

Reaction notes

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