Methane → HCID 68125504, compound

HRID 839602Notes

Reaction equation

HRID 839602 reaction equation
C(O[CH:4](OCC)[CH2:5][NH:6][C:7]1[N:11]([CH3:12])[N:10]=[N:9][N:8]=1)C.[ClH:16].[OH:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[OH:27])[CH2:21][CH2:22][NH2:23].Cl.C>O.C(O)C>[ClH:16].[CH3:12][N:11]1[C:7]([NH:6][CH2:5][CH:4]2[C:24]3[C:20](=[CH:19][C:18]([OH:17])=[C:26]([OH:27])[CH:25]=3)[CH2:21][CH2:22][NH:23]2)=[N:8][N:9]=[N:10]1

Participants

7

Reactant 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 65340Dopamine HydrochlorideHCID 13139802N-(2,2-Diethoxyethyl)-1-methyl-1H-tetrazol-5-amine

Product 1

HCID 68125504HCID 68125504, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

(1-methyl-1H-tetrazol-5-yl)aminoacetaldehyde diethyl acetal (21.5 g.) and 3,4-dihydroxyphenethylamine hydrochloride (14.6 g.) were added to a mixture of ethanol (130 ml.) and water (35 ml.), and dissolved with heating and stirring. Conc. hydrochloric acid (10.5 ml.) was added thereto and the mixture was refluxed for 8 hours. The reaction mixture was treated with activated charcoal. The charcoal was filtered and washed with ethanol, after which the filtrate and the washings were combined and concentrated under reduced pressure. The residual crystals were recrystallized from a mixture of water and isopropyl alcohol and the obtained crystals (22.5 g.) were warmed for 16 hours at 60° C under reduced pressure to remove excess hydrogen chloride. The crystals were recrystallized from a mixture of a small amount of water, methanol and ether to give 1-(1-methyl-1H-tetrazol-5-yl)aminomethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride trihemihydrate (15 g.), mp 107° to 110° C. Infrared Absorption Spectrum (Nujol) 1604, 1460 cm-1.

Workup

  1. dissolutiondissolved
  2. temperaturewith heating
  3. temperaturethe mixture was refluxed for 8 hours
  4. filtrationThe charcoal was filtered
  5. washwashed with ethanol
  6. concentrationconcentrated under reduced pressure
  7. customThe residual crystals were recrystallized from a mixture of water and isopropyl alcohol
  8. customto remove excess hydrogen chloride
  9. customThe crystals were recrystallized from a mixture of a small amount of water, methanol and ether

Sources & evidence

ORD record
ord-dfc30cbb62c842dfa8f0fddcbe147968
Source dataset
uspto-grants-1978_06
Patent number
US04096263

Reaction notes

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