Sodium Bicarbonate → 1-(N-benzyloxycarbonyl-p-benzyloxyanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline

HRID 543739Notes

Reaction equation

HRID 543739 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([O:19][C:20]([N:22]([CH2:37][CH:38]1[C:47]2[C:42](=[CH:43][C:44]([OH:49])=[C:45]([OH:48])[CH:46]=2)[CH2:41][CH2:40][NH:39]1)[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:25][CH:24]=1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)(O)[O-].[Na+]>>[CH2:12]([O:19][C:20]([N:22]([CH2:37][CH:38]1[C:47]2[C:42](=[CH:43][C:44]([OH:49])=[C:45]([OH:48])[CH:46]=2)[CH2:41][CH2:40][NH:39]1)[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:25][CH:24]=1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 516892Sodium BicarbonateHCID 204605141-(N-benzyloxycarbonyl-p-benzyloxyanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline p-toluenesulfonate

Product 1

HCID 204605151-(N-benzyloxycarbonyl-p-benzyloxyanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolineYield 109.7%

Procedure

To 1-(N-benzyloxycarbonyl-p-benzyloxyanilinomethyl)-6.7-dihydroxy-1,2,3,4-tetrahydroisoquinoline p-toluenesulfonate (10.0 g) was added a saturated sodium bicarbonate aqueous solution and then the mixture was extracted with ethyl acetate. The extract was washed with water, dried and the solvent was distilled off to give 1-(N-benzyloxycarbonyl-p-benzyloxyanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (8.2 g). To this residue (8.2 g) were added conc. hydrochloric acid (50 ml) and ethanol (50 ml) and the mixture was refluxed for 4 hours with stirring. The reaction mixture was concentrated to dryness under reduced pressure and the residue was pulverized with ether to give a powder of 1-(p-hydroxyanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline dihydrochloride (5.8 g), mp 170° to 184° C. (dec).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-0251780aba91485d9de62f86bb373895
Source dataset
uspto-grants-1984_05
Patent number
US04447436

Reaction notes

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