Diethyl Ether → 5-Bromo-2-hydroxy-6-(piperidine-1-yl)-benzo[de]isoquinoline-1,3-dione

HRID 279014Notes

Reaction equation

HRID 279014 reaction equation
C([O:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[C:21]([Br:29])[C:22]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[C:15]3[C:16]=2[C:11](=[CH:12][CH:13]=[CH:14]3)[C:10]1=[O:30])C1C=CC=CC=1.FC(F)(F)C([O-])=O.FC(F)(F)C([O-])=O.FC(F)(F)C([O-])=O.[B+3].C(OCC)C>C(O)(C(F)(F)F)=O>[Br:29][C:21]1[C:22]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:16]2=[C:17]([CH:20]=1)[C:18](=[O:19])[N:9]([OH:8])[C:10]3=[O:30]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 226239132-Benzyloxy-5-bromo-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dioneHCID 178525683HCID 178525683, compound

Product 1

HCID 226240335-Bromo-2-hydroxy-6-(piperidine-1-yl)-benzo[de]isoquinoline-1,3-dioneYield 27.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-benzyloxy-5-bromo-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione (0.27 g, 0.58 mmol, from Example T1-A) in TFA (5 mL) at 0° C. was added a 1.0 M solution of boron tris(trifluoroacetate) in TFA (3 mL). The reaction was stirred at 0° C. for 2 hours. Ethyl ether was added forming a precipitate which was collected by filtration. The solid was taken up in chloroform, the organic layer washed with water, dried, filtered, and evaporated under reduced pressure to give 0.060 g of the title compound as the TFA salt, mp >250° C.

Workup

  1. customat 0° C.
  2. customforming a precipitate which
  3. filtrationwas collected by filtration
  4. washthe organic layer washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a1e8b716a6484ca9911a748dc98b172f
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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