Boron Trichloride → 6-Methoxy-1-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-ol

HRID 1513909Notes

Reaction equation

HRID 1513909 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH3:14])[CH:9]=2)[C:4]=1[C:15]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:19][CH:18]=1)=[O:16].B(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[OH:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH3:14])[CH:9]=2)[C:4]=1[C:15]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:19][CH:18]=1)=[O:16]

Participants

5

Reactant 3

HCID 25135Boron Trichloride2×HCID 516892Sodium BicarbonateHCID 11654660(2,6-Dimethoxy-naphthalen-1-yl)-[4-(2-piperidin-1-yl-ethoxy)phenyl]-methanone

Product 1

HCID 219316286-Methoxy-1-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-olYield 99%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve (2,6-dimethoxy-naphthalen-1-yl)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (56.0 g, 123 mmol) in chloroform (500 mL). Cool to 0° C. Add boron trichloride (150 mL, 150 mmol, 1 M solution in dichloromethane) and stir 2 hours. Warm to room temperature and stir 1.5 hours. Add additional boron trichloride (50 mL, 50 mmol) after cooling to 0° C. Warm to room temperature and stir overnight. Carefully add ice and saturated aqueous sodium bicarbonate. Separate organic and wash aqueous three times with a 3:1 dichloromethane:isopropanol mixture. Concentrate in vacuo and dissolve in dichloromethane. Dry over sodium sulfate, decant, and concentrate in vacuo. Slurry in ether and filter, rinsing with hexanes to give 49.4 g of (2-hydroxy-6-methoxy-naphthalen-1-yl)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (99%).

Workup

  1. temperatureWarm to room temperature
  2. temperatureafter cooling to 0° C
  3. temperatureWarm to room temperature
  4. stirringstir overnight
  5. washSeparate organic and wash aqueous three times with a 3:1 dichloromethane
  6. concentrationConcentrate in vacuo
  7. dissolutiondissolve in dichloromethane
  8. dry with materialDry over sodium sulfate
  9. customdecant
  10. concentrationconcentrate in vacuo
  11. filtrationfilter
  12. washrinsing with hexanes

Sources & evidence

ORD record
ord-0328ba7189db4a698d10084216670626
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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