5-(Benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinoline → HCID 83875098, compound

HRID 717368Notes

Reaction equation

HRID 717368 reaction equation
C([O:8][C:9]1[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][NH:13][CH2:14]2)C1C=CC=CC=1>[C].[Pd].CO>[OH:8][C:9]1[C:18]([O:19][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 214470265-(Benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 83875098HCID 83875098, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Into a 50-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed Palladium carbon (10%) (200 mg), methanol (10 mL) and 5-(benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinoline (800 mg, 2.97 mmol, 1.00 equiv). To the above H2 (enough, amount) was introduced in. The resulting solution was stirred for 2 h at room temperature. The solids were filtered out. The resulting solution was diluted with 12 mL of tetrahydrofuran. To this was HCl (gas) (enough amount) was introduced in. The resulting mixture was concentrated under vacuum. The solids were collected by filtration. The filter cake was washed with 2×20 mL of dichloromethane. This resulted in 0.5 g (crude) of 5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride as a off-white solid. 1H NMR (300 MHz, DMSO-d6) δ 2.88-3.92 (t, 2H), 3.40-3.44 (t, 2H), 3.77 (s, 3H), 4.20 (s, 2H), 6.68-6.70 (d, 1H), 6.88-6.91 (d, 1H); MS (ESI) m/z 180 ([M+H]+).

Workup

  1. customInto a 50-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. additionTo the above H2 (enough, amount) was introduced in
  4. filtrationThe solids were filtered out
  5. additionThe resulting solution was diluted with 12 mL of tetrahydrofuran
  6. additionTo this was HCl (gas) (enough amount) was introduced in
  7. concentrationThe resulting mixture was concentrated under vacuum
  8. filtrationThe solids were collected by filtration
  9. washThe filter cake was washed with 2×20 mL of dichloromethane
  10. customThis resulted in 0.5 g (crude) of 5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride as a off-white solid

Sources & evidence

ORD record
ord-881623c5a81a4a6488fa13422b0767aa
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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