HCID 90411330, compound → 6-(Dimethylamino)-1,2,3,4-tetrahydro-5-isoquinolinol

HRID 717381Notes

Reaction equation

HRID 717381 reaction equation
C([O:8][C:9]1[C:18]([N:19]([CH3:21])[CH3:20])=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][N:13](C(OCC1C=CC=CC=1)=O)[CH2:14]2)C1C=CC=CC=1>[C].[Pd].CO>[OH:8][C:9]1[C:18]([N:19]([CH3:21])[CH3:20])=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][NH:13][CH2:14]2

Participants

4

Reactant 1

HCID 90411330HCID 90411330, compound

Product 1

HCID 904104316-(Dimethylamino)-1,2,3,4-tetrahydro-5-isoquinolinol

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed methanol (40 mL), Palladium carbon (400 mg) and benzyl 5-(benzyloxy)-6-(dimethylamino)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (1.6 g, 3.84 mmol, 1.00 equiv). To the above H2 gas was introduced in. The resulting solution was stirred overnight at 25° C. The solids were filtered out. The resulting mixture was concentrated under vacuum. This resulted in 1 g (crude) of 5-hydroxy-6-dimethylamino-1,2,3,4-tetrahydroisoquinoline as brown oil. MS (ESI) m/z 193 ([M+H]+).

Workup

  1. customInto a 100-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. additionTo the above H2 gas was introduced in
  4. filtrationThe solids were filtered out
  5. concentrationThe resulting mixture was concentrated under vacuum
  6. customThis resulted in 1 g (crude) of 5-hydroxy-6-dimethylamino-1,2,3,4-tetrahydroisoquinoline as brown oil

Sources & evidence

ORD record
ord-6e2dc70156564c1f99d1eda122fca137
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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