Hydrochloric Acid → 1-(N-isopropylaminomethyl)-7,8-dihydroxy-1,2,3,4-tetrahydroisoquinoline dihydrochloride

HRID 27160Notes

Reaction equation

HRID 27160 reaction equation
[ClH:1].C(OC([N:12]([CH2:16][CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([OH:28])[C:25]=2[OH:27])[CH2:20][CH2:19][NH:18]1)[CH:13]([CH3:15])[CH3:14])=O)C1C=CC=CC=1.Cl>C(O)(=O)C>[ClH:1].[ClH:1].[CH:13]([NH:12][CH2:16][CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([OH:28])[C:25]=2[OH:27])[CH2:20][CH2:19][NH:18]1)([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 204605571-(N-benzyloxycarbonyl-N-isopropylaminomethyl)-7,8-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 204605471-(N-isopropylaminomethyl)-7,8-dihydroxy-1,2,3,4-tetrahydroisoquinoline dihydrochloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-(N-benzyloxycarbonyl-N-isopropylaminomethyl)-7,8-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (1.1 g), acetic acid (11 ml) and conc. hydrochloric acid (11 ml) was refluxed for 1.5 hours. The reaction mixture was concentrated to dryness under reduced pressure and the residue was washed with acetone, followed by recrystallization from a mixture of methanol and ether to give 1-(N-isopropylaminomethyl)-7,8-dihydroxy-1,2,3,4-tetrahydroisoquinoline dihydrochloride, colorless crystals, mp 255° to 258° C.

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  3. washthe residue was washed with acetone
  4. customfollowed by recrystallization from a mixture of methanol and ether

Sources & evidence

ORD record
ord-4d076c1611314d98aaec6d400c7dbd84
Source dataset
uspto-grants-1980_09
Patent number
US04220647

Reaction notes

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