Hydrochloric Acid → HCID 15314191, compound

HRID 1416359Notes

Reaction equation

HRID 1416359 reaction equation
Cl.C(OC([N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[O:19][CH2:20][CH3:21])[CH2:10]1)=O)(C)(C)C>C(O)C>[CH2:20]([O:19][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:16]=1[CH2:17][CH2:18][NH:9][CH2:10]2)[CH3:21]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 154342991,1-Dimethylethyl 5-ethoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Product 1

HCID 15314191HCID 15314191, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Excess of 3 mol L-1 hydrochloric acid in ethanol was added to a solution of 2-t-butoxycarbonyl-5-ethoxy-1,2,3,4-tetrahydroisoquinoline (Example 8) (1.55 g, 5.6 mmol) in ethanol. After 3 hours, the solution was evaporated to dryness, and the hydrochloride salt of 5-ethoxy-1,2,3,4-tetrahydroisoquinoline was dissolved in water. The solution was made strongly alkaline with sodium hydroxide, and the product was extracted in dichloromethane, dried over Na2SO4, and evaporated. The product was purified by recrystallization from absolute ethanol. Yield 0.69 g, 71%. 1H NMR (DMSO-d6, 500 MHz): 7.02 (1H, t, 7.8 Hz). 6.70 (1H, d, 8.0 Hz), 6.57 (1H, d, 7.2 Hz), 3.98 (2H, q, 6.9 Hz), 3.77 (2H, s), 3.24 (2H, s), 2.91 (2H, s), 1.31 (3H, t, 6.9 Hz); 13C NMR (DMSO-d6, 120 MHz): 156.1, 137.5, 125.7, 123.5, 118.1, 108.2, 62.9, 47.7, 43.0, 23.1, 14.7; MS(EI+): 177 (95%, M+), 148 (100%), 132 (25%), 120 (43%), 104 (56%), 91 (33%).

Workup

  1. customthe solution was evaporated to dryness
  2. dissolutionthe hydrochloride salt of 5-ethoxy-1,2,3,4-tetrahydroisoquinoline was dissolved in water
  3. extractionthe product was extracted in dichloromethane
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe product was purified by recrystallization from absolute ethanol

Sources & evidence

ORD record
ord-71eb29ad43d24408a67aaef80eee7b77
Source dataset
uspto-grants-1999_06
Patent number
US05912342

Reaction notes

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