Hydrochloric Acid → N-propyl-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamine

HRID 1262862Notes

Reaction equation

HRID 1262862 reaction equation
Cl.[CH2:2]([NH2:5])[CH2:3][CH3:4].[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH2:14][C:13](=O)[CH2:12][CH2:11]2.C([BH3-])#N.[Na+].Cl.[OH-].[Na+]>CO>[CH2:2]([NH:5][CH:13]1[CH2:12][CH2:11][C:10]2[C:15](=[CH:16][CH:17]=[C:8]([O:7][CH3:6])[CH:9]=2)[CH2:14]1)[CH2:3][CH3:4]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 11165Propylamine hydrochlorideHCID 14798Sodium HydroxideHCID 755826-Methoxy-1,2,3,4-tetrahydronaphthalen-2-oneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 10242549N-propyl-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamineYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

Propylamine hydrochloride (169 g, 1.8 mol) was dissolved in methanol (370 mL) and 6-methoxy-2-tetralone (50 g, 0.28 mol) was added. Thereafter, sodium cyanoborohydride (44.2 g, 0.7 mol) was added portionwise with cooling. During the latter addition, the temperature of the reaction mixture was kept at 20° C. to minimize foaming. The resulting suspension was stirred at room temperature (25° C.) for 18 hr. Excess hydrochloric acid (1:1) was added and the white suspension was cooled in ice. The solid was collected on a filter and washed with methanol (3×200 mL) to give 92 g of crude product. The crude product was treated with 10% (w/v) sodium hydroxide and extracted with benzene. The organic extract was dried and evaporated to give a pale yellow oil (31.93 g) of N-propyl-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamine, NMR (CDCl3) δ 0.90 (t, 3H), 1.15 (s, 1H), 1.50 (m, 2H), 3.70 (s, 3H), 6.55 (s, 1H), 6.60 (d, 1H) and 6.90 (d, 1H).

Workup

  1. temperaturewith cooling
  2. additionDuring the latter addition
  3. customwas kept at 20° C.
  4. temperaturethe white suspension was cooled in ice
  5. customThe solid was collected on
  6. filtrationa filter
  7. washwashed with methanol (3×200 mL)
  8. customto give 92 g of crude product
  9. extractionextracted with benzene
  10. extractionThe organic extract
  11. customwas dried
  12. customevaporated

Sources & evidence

ORD record
ord-094e1f3db5834ae2b73775f34fb70ace
Source dataset
uspto-grants-1984_06
Patent number
US04454150

Reaction notes

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