Water → HCID 69083292, compound

HRID 594660Notes

Reaction equation

HRID 594660 reaction equation
C[O:2][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[C:5]([O:12][CH3:13])[C:4]=1[CH:14]1[N:19]([CH2:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=2)[C:18](=[O:31])[CH2:17][CH2:16][CH2:15]1.O>C(Cl)Cl>[OH:2][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[C:5]([O:12][CH3:13])[C:4]=1[CH:14]1[N:19]([CH2:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=2)[C:18](=[O:31])[CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 962WaterHCID 69082468HCID 69082468, compound

Product 1

HCID 69083292HCID 69083292, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-(2,6-dimethoxy-3-nitrophenyl)-1-(quinolin-2-ylmethyl)piperidin-2-one (403 mg; 0.95 mmol) in anh. DCM (9 ml) was treated dropwise at rt with a solution of boron tribromide BBr3 (1 M in DCM; 4.4 ml; 4.4 mmol). The resulting mixture was further stirred at rt, under nitrogen, for 17 h. Water and ice were added, and the separated aq. layer was extracted with DCM. The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Subsequent purification by FC (DCM/MeOH=30/1) afforded 6-(2-hydroxy-6-methoxy-3-nitrophenyl)-1-(quinolin-2-ylmethyl)-piperidin-2-one as a yellow solid (340 mg; 87%). LC-MS (conditions A): tR=0.60 min.; [M+H]+: 407.82 g/mol.

Workup

  1. extractionthe separated aq. layer was extracted with DCM
  2. washThe mixed organic layers were washed with brine
  3. dry with materialdried over anh. MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customSubsequent purification by FC (DCM/MeOH=30/1)

Sources & evidence

ORD record
ord-a94e68a72d6d4edcbaf7fa5b7437ecd7
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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