Hydrochloric Acid → 5,6-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 717372Notes

Reaction equation

HRID 717372 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][N:7](C(OC(C)(C)C)=O)[CH2:8]2.[ClH:22]>CO>[ClH:22].[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][NH:7][CH2:8]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90410651tert-butyl 5,6-dimethoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 717574045,6-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a 50-mL round-bottom flask, was placed a solution of tert-butyl 5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (800 mg, 2.73 mmol, 1.00 equiv) in methanol (15 mL) and hydrogen chloride (4 mL). The resulting solution was stirred for 5 h at room temperature. The resulting mixture was concentrated under vacuum. The residue was diluted with 5 mL of water. The resulting mixture was extracted with 3×30 mL of ethyl acetate and the aqueous layer combined. The mixture was concentrated under vacuum. This resulted in 500 mg (80%) of 5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride as a white solid. MS (ESI) m/z 194 ([M+H]+).

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. additionThe residue was diluted with 5 mL of water
  4. extractionThe resulting mixture was extracted with 3×30 mL of ethyl acetate
  5. concentrationThe mixture was concentrated under vacuum
  6. customThis resulted in 500 mg (80%) of 5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride as a white solid

Sources & evidence

ORD record
ord-c7af02df6d864ddf9939bf2877c5e11e
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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