Hydrochloric Acid → HCID 12868344, compound

HRID 1156157Notes

Reaction equation

HRID 1156157 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH:5]1[CH:10]=[C:9]([O:11]C)[CH2:8][C:7]([O:13]C)=[CH:6]1.Cl>O1CCCC1.O>[CH3:1][NH:2][CH2:3][CH2:4][CH:5]1[CH2:6][C:7](=[O:13])[CH2:8][C:9](=[O:11])[CH2:10]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 128664463,5-Dimethoxy-N-methyl-2,5-cyclohexadiene-1-ethanamine

Product 1

HCID 12868344HCID 12868344, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of N-methyl-1,5-dimethoxycyclohexa-1,4-diene-3-ethylamine (5.5 g, 27.9 mmol) in 20 ml of tetrahydrofuran was added 10 ml of 6 N hydrochloric acid in one portion. The warm solution was heated for 15 min. at 50° C. and concentrated to give a light yellow oil. The crude oil was dissolved in 25 ml of water, and the solution was mixed with 50 g of Dowex 50X8 resin (previously washed with 2 N HCl and deionized water) in a sintered glass funnel. After a few minutes, the aqueous solution was drawn out by suction, and the resin rinsed with four 50 ml-portions of water, and then with eight 35 ml-portions of 2 M aqueous pyridine. Pyridine fractions 3-8 were pooled and concentrated to give 3.9 g of 5-[(2-methylamino)ethyl]-cyclohexane-1,3-dione. An analytical sample crystallized from water and had mp 171°-4° C.

Workup

  1. concentrationconcentrated
  2. customto give a light yellow oil
  3. additionthe solution was mixed with 50 g of Dowex 50X8 resin (
  4. washpreviously washed with 2 N HCl and deionized water) in a sintered glass funnel
  5. waitAfter a few minutes
  6. washthe resin rinsed with four 50 ml-portions of water
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fcbcbb686f6d408ea7f4acb04d8382b9
Source dataset
uspto-grants-1982_06
Patent number
US04334070

Reaction notes

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