Sodium Hydroxide → HCID 67749524, compound

HRID 2270508Notes

Reaction equation

HRID 2270508 reaction equation
[ClH:1].C[O:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[C@@H:12]([CH2:14][CH2:15][CH3:16])[C@@H:11]([NH:17][CH2:18][CH2:19][CH3:20])[CH2:10][CH2:9]2.CON.[OH-].[Na+]>Br>[ClH:1].[CH2:14]([C@H:12]1[C:13]2[C:4]([OH:3])=[CH:5][CH:6]=[CH:7][C:8]=2[CH2:9][CH2:10][C@H:11]1[NH:17][CH2:18][CH2:19][CH3:20])[CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67749549HCID 67749549, compound

Product 1

HCID 67749524HCID 67749524, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 0.57 g (2.0 mmol) methoxy-amine cis(±)-1,2,3,4-tetrahydro-8-methoxy-N,1-di-propyl-2-naphthalenamine hydrochloride in 10 mL 48% hydrobromic acid was refluxed (bath temperature, 120° C.) for eight hours. TLC analysis showed no starting material remaining. The mixture was cooled to room temperature, treated with 20% sodium hydroxide to pH 7-8, and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The oil was converted to HCl-salt with excess anhydrous hydrochloric acid and recrystallized from ethyl acetate to give 0.36 g (64%) of pure title compound as a white solid: m.p. 244°-245° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-852735b805744b889ef94f259ac49ec4
Source dataset
uspto-grants-2001_12
Patent number
US06331636B1

Reaction notes

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