Methanol → 1-(Biphenyl-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol hydrochloride

HRID 2238352Notes

Reaction equation

HRID 2238352 reaction equation
[ClH:1].C([O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[O:20]CC1C=CC=CC=1)[CH:16]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:31][CH:30]=1)[NH:15][CH2:14][CH2:13]2)C1C=CC=CC=1.CO>Cl>[ClH:1].[OH:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[OH:20])[CH:16]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:31][CH:30]=1)[NH:15][CH2:14][CH2:13]2

Participants

4

Reactant 2

HCID 887MethanolHCID 160865076,7-Bis-benzyloxy-1-biphenyl-4-ylmethyl-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 160865021-(Biphenyl-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol hydrochloride

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

6,7-bis-hydroxy-1-biphenyl-4-ylmethyl-1,2,3,4-tetrahydro-isoquinoline hydrochloride (3) was prepared as follows: A stirred mixture of 2.5 g (4.56 mmol) of 6,7-bis-benzyloxy-1-biphenyl-4-ylmethyl-1,2,3,4-tetrahydro-isoquinoline hydrochloride in 10 ml of concentrated aqueous HCl solution/10 ml of methanol was refluxed for 10 hours. The solvents were evaporated under reduced pressure, the solid residue was mixed with 10 ml of ether and separated on a glass filter funnel, and then washed with ether (2×10 ml). This solid was recrystallized using ether/methanol mixture to give 1.3 g (78%) of off-white crystals, mp 208-210° C.

Workup

  1. temperaturewas refluxed for 10 hours
  2. customThe solvents were evaporated under reduced pressure
  3. additionthe solid residue was mixed with 10 ml of ether
  4. customseparated on a glass
  5. filtrationfilter funnel
  6. washwashed with ether (2×10 ml)
  7. customThis solid was recrystallized

Sources & evidence

ORD record
ord-e77ef0d4ebe24814a0b6166c95c70e38
Source dataset
uspto-grants-2010_05
Patent number
US07718672B2

Reaction notes

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