Hydrochloric Acid → 1-Aminomethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline dihydrochloride

HRID 27162Notes

Reaction equation

HRID 27162 reaction equation
[ClH:1].C(OC([NH:12][CH2:13][CH:14]1[C:23]2[C:18](=[CH:19][C:20]([OH:25])=[C:21]([OH:24])[CH:22]=2)[CH2:17][CH2:16][NH:15]1)=O)C1C=CC=CC=1.Cl>C(O)(=O)C>[ClH:1].[ClH:1].[NH2:12][CH2:13][CH:14]1[C:23]2[C:18](=[CH:19][C:20]([OH:25])=[C:21]([OH:24])[CH:22]=2)[CH2:17][CH2:16][NH:15]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 204605221-(N-benzyloxycarbonylaminomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 128577221-Aminomethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline dihydrochlorideYield 61.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-(N-benzyloxycarbonylaminomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (5.3 g), conc. hydrochloric acid (6 ml) and acetic acid (6 ml) was refluxed for 1 hour and 20 minutes. The reaction mixture was cooled and concentrated under reduced pressure. The residue was crystallized by adding methanol and acetone. The crystals were collected by filtration, washed with a mixture of methanol and acetone and recrystallized twice from a mixture of water, methanol and acetone to give 1-aminomethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline dihydrochloride (1.2 g), mp 142° to 147° C. (dec).

Workup

  1. temperaturewas refluxed for 1 hour and 20 minutes
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was crystallized
  5. additionby adding methanol and acetone
  6. filtrationThe crystals were collected by filtration
  7. washwashed with a mixture of methanol and acetone
  8. customrecrystallized twice from a mixture of water, methanol and acetone

Sources & evidence

ORD record
ord-22b38e9f01b44835bc68ef1bbc35f19a
Source dataset
uspto-grants-1980_09
Patent number
US04220647

Reaction notes

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