Hydrogen Bromide → JWH 018 5-hydroxyindole metabolite

HRID 55926Notes

Reaction equation

HRID 55926 reaction equation
Br.C[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:8]=[C:7]2[C:18]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)=[O:19]>O>[OH:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:8]=[C:7]2[C:18]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)=[O:19]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 681592935-methoxy-3-(1-naphthoyl)-N-pentyl-1H-indole

Product 1

HCID 53394447JWH 018 5-hydroxyindole metaboliteYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of hydrobromic acid (48 w/w/%) in water (150 ml) was added 5 (6.5 g, 17.5 mmol) and the mixture was heated at reflux for 3 h. The solution was cooled to room temperature and concentrated to dryness. Water was then added (200 ml), the solution neutralized to pH 7-8 and then extracted with ethyl acetate (3×150 ml). The combined organic layers were washed by water (150 ml), brine (150 ml), dried over Na2SO4, filtered and concentrated to dryness. The crude product was then recrystallized from ethyl acetate/hexane to give a white solid of 5-hydroxy-3-(1-naphthoyl)-N-pentyl-1H-indole 6 (4.5 g, 72%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 h
  3. concentrationconcentrated to dryness
  4. additionWater was then added (200 ml)
  5. extractionextracted with ethyl acetate (3×150 ml)
  6. washThe combined organic layers were washed by water (150 ml), brine (150 ml)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. customThe crude product was then recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-4f97f2ce07dd436e86a05978840ba68f
Source dataset
uspto-grants-2016_09
Patent number
US09434687B2

Reaction notes

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