Nitrogen → Trifluoromethanesulfonic acid 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)benzoyl]-naphthalen-2-yl ester

HRID 2223678Notes

Reaction equation

HRID 2223678 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[C:3]=1[C:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:18][CH:17]=1)=[O:15].N#N.N1C=CC=CC=1.[F:39][C:40]([F:46])([F:45])[S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl>[CH3:13][O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[C:3]([C:14](=[O:15])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:18][CH:17]=1)=[C:2]([O:1][S:41]([C:40]([F:46])([F:45])[F:39])(=[O:43])=[O:42])[CH:11]=[CH:10]2

Participants

6

Reactant 4

HCID 947NitrogenHCID 1049PyridineHCID 79000Trifluoromethanesulfonyl chlorideHCID 219316286-Methoxy-1-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-ol

Product 1

HCID 11685250Trifluoromethanesulfonic acid 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)benzoyl]-naphthalen-2-yl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve (2-hydroxy-6-methoxy-naphthalen-1-yl)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone in CH2Cl2 (10 volumes) in a three neck round bottom flask equipped with a stir bar and N2 source and chill to 0° C. in an ice/brine bath. Add pyridine (1.3 equivalents). Add trifluoromethane sulfonyl chloride (1.2 equivalents) via syringe over 15 minutes. The yellow slurry turns clear orange with this addition. The reaction is determined to be complete by HPLC analysis after 15 minutes. Quench the reaction with H2O (10 volumes), wash with 1 N HCl (5 volumes), wash with 1.0 N NaHCO3, and dry over Na2SO4. After concentration, trifluoro-methanesulfonic acid 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-yl ester as a clean yellow foam is obtained in quantitative yield. Use the product without further purification.

Workup

  1. customequipped with a stir bar
  2. additionThe yellow slurry turns clear orange with this addition
  3. customQuench
  4. customthe reaction with H2O (10 volumes)
  5. washwash with 1 N HCl (5 volumes)
  6. washwash with 1.0 N NaHCO3
  7. dry with materialdry over Na2SO4
  8. concentrationAfter concentration

Sources & evidence

ORD record
ord-dad7c2f017e64f2485d343e4ec3da26f
Source dataset
uspto-grants-2008_05
Patent number
US07375229B2

Reaction notes

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