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

HRID 543736Notes

Reaction equation

HRID 543736 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-4398a738072e43ca88696b5d2f36df9c
Source dataset
uspto-grants-1984_05
Patent number
US04447436

Reaction notes

Loading…