Hydrochloric Acid → HCID 20323730, compound

HRID 839613Notes

Reaction equation

HRID 839613 reaction equation
Cl.[OH:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[OH:12])[CH2:6][CH2:7][NH2:8].C(O[CH:16](OCC)[CH2:17][NH:18][C:19]1[NH:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1)C.Cl.C(=O)(O)[O-].[Na+].[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]/[C:40]([OH:42])=[O:41]>C(O)CCC.O.CO>[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]/[C:40]([OH:42])=[O:41].[N:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[NH:23][C:19]=1[NH:18][CH2:17][CH:16]1[C:9]2[C:5](=[CH:4][C:3]([OH:2])=[C:11]([OH:12])[CH:10]=2)[CH2:6][CH2:7][NH:8]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 65340Dopamine HydrochlorideHCID 444972Fumaric AcidHCID 516892Sodium BicarbonateHCID 85893810HCID 85893810, compound

Product 1

HCID 20323730HCID 20323730, compoundYield 85.5%

Reagents, catalysts & solvents 3

HCID 2631-ButanolSolventHCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
110 °C

Procedure

A solution of 3,4-dihydroxyphenethylamine hydrochloride (1.37 g.), 2-benzimidazolylaminoacetaldehyde diethyl acetal (2.0 g.) and conc. hydrochloric acid (0.8 ml.) in a mixture of n-butanol (7 ml.) and water (3 ml.) was stirred for 10 hours at 110° C. The reaction mixture was allowed to stand at ambient temperature and precipitating crystals were collected by filtration and washed with a mixture of methanol and ether to give crystals (2.92 g.). The crystals were dissolved in water and the solution was neutralized by adding sodium bicarbonate and extracted 3 times with methyl ethyl ketone. The combined extracts were washed with a saturated sodium chloride aqueous solution and dried over magnesium sulfate. The solvent was distilled off to give oil, which was dissolved in methanol (10 ml.). Fumaric acid (0.7 g.) was added thereto and the mixture was stirred and allowed to stand to precipitate crystals. The crystals were collected by filtration and washed with methanol to give 1-(2-benzimidazolyl)aminomethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline fumarate (2.2 g.). This material was recrystallized from a mixture of dimethylsulfoxide and water to give pure compound (1.0 g.), mp 257° to 259° C (dec.).

Workup

  1. customto stand at ambient temperature
  2. customprecipitating crystals
  3. filtrationwere collected by filtration
  4. washwashed with a mixture of methanol and ether
  5. customto give crystals (2.92 g.)
  6. extractionextracted 3 times with methyl ethyl ketone
  7. washThe combined extracts were washed with a saturated sodium chloride aqueous solution
  8. dry with materialdried over magnesium sulfate
  9. distillationThe solvent was distilled off
  10. customto give oil, which
  11. stirringthe mixture was stirred
  12. customto precipitate crystals
  13. filtrationThe crystals were collected by filtration
  14. washwashed with methanol

Sources & evidence

ORD record
ord-96f9da513e3e4f608e9d271c353d7216
Source dataset
uspto-grants-1978_06
Patent number
US04096263

Reaction notes

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