Hydrochloric Acid → HCID 12857726, compound

HRID 543735Notes

Reaction equation

HRID 543735 reaction equation
[ClH:1].C(OC([N:12]([CH2:16][CH:17]1[C:26]2[C:21](=[CH:22][C:23]([OH:28])=[C:24]([OH:27])[CH:25]=2)[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][C:23]([OH:28])=[C:24]([OH:27])[CH:25]=2)[CH2:20][CH2:19][NH:18]1)([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20460574HCID 20460574, compound

Product 1

HCID 12857726HCID 12857726, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-(N-benzyloxycarbonyl-N-isopropylaminomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (3.5 g), conc. hydrochloric acid (20 ml) and acetic acid (20 ml) was refluxed for 1 hour. The reaction mixture was concentrated to dryness under reduced pressure and the residue was crystallized with a mixture of acetone and water. The crystals were recrystallized from a mixture of methanol and ether to give 1-(N-isopropylaminomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline dihydrochloride (1.15 g), mp 268° to 270° C. (dec).

Workup

  1. temperaturewas refluxed for 1 hour
  2. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  3. customthe residue was crystallized with a mixture of acetone and water
  4. customThe crystals were recrystallized from a mixture of methanol and ether

Sources & evidence

ORD record
ord-3d7cc29f7318450496abf132d8e02825
Source dataset
uspto-grants-1984_05
Patent number
US04447436

Reaction notes

Loading…