Water → HCID 117701716, compound

HRID 1507447Notes

Reaction equation

HRID 1507447 reaction equation
[OH:1][C:2]1[C:11]([CH:12]=[O:13])=[C:10]2[C:5]([C:6](=[O:25])[C:7]([CH3:24])=[C:8]([CH:14]3[CH2:19][CH2:18][N:17]([C:20](=[O:23])[CH2:21][CH3:22])[CH2:16][CH2:15]3)[O:9]2)=[CH:4][CH:3]=1.[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:26]([O:1][C:2]1[C:11]([CH:12]=[O:13])=[C:10]2[C:5]([C:6](=[O:25])[C:7]([CH3:24])=[C:8]([CH:14]3[CH2:15][CH2:16][N:17]([C:20](=[O:23])[CH2:21][CH3:22])[CH2:18][CH2:19]3)[O:9]2)=[CH:4][CH:3]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 117701619HCID 117701619, compound

Product 1

HCID 117701716HCID 117701716, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7-hydroxy-3-methyl-4-oxo-2-(1-propanoylpiperidin-4-yl)-4H-chromene-8-carbaldehyde (250 mg, 0.73 mmol) obtained in Example 34-1, benzyl bromide (260 μL, 3.64 mmol), and potassium carbonate (503 mg, 3.64 mmol) in dimethylformamide (4 mL) was stirred at room temperature for 26 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and then dried over sodium sulfate. The desiccant was filtered off, and then the filtrate was concentrated under reduced pressure. Diethyl ether and n-hexane were added to the obtained residue. Then, the supernatant was removed by decantation to obtain 305 mg of the title compound (yield: 97%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationThe desiccant was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionDiethyl ether and n-hexane were added to the obtained residue
  7. customThen, the supernatant was removed by decantation

Sources & evidence

ORD record
ord-906d11c3c5c74cf6a7910e2fb8dcc37d
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

Loading…