Dimethylformamide → HCID 18770930, compound

HRID 1786825Notes

Reaction equation

HRID 1786825 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:12]2[CH2:17][C:16]3([CH:22]=C[C:20]4[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=4[O:18]3)[CH2:15]CN2CC(OCC)=O)[CH:5]=[C:6](F)[C:7]=1[O:8]CC.[C:33](=[O:36])([O-])[OH:34].[Na+].[CH2:38](I)[CH3:39].[CH3:41][N:42]([CH3:45])[CH:43]=O>C(OCC)(=O)C>[OH:8][C:7]1[CH:6]=[CH:5][C:4]([C:12]2[C:20]3[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=3[O:18][C:16]3([CH2:22][CH2:43][N:42]([CH2:45][C:33]([O:34][CH2:38][CH3:39])=[O:36])[CH2:41][CH2:15]3)[CH:17]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 516892Sodium BicarbonateHCID 131724208HCID 131724208, compound

Product 1

HCID 18770930HCID 18770930, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0.800000011920929 °C

Procedure

To a mixture of 1′-carboxymethyl-4-(4-hydroxyphenyl)spiro[2H-1-benzopyran-2,4′-piperidine]-1′-acetate (432 mg, 1 mmol., prepared according to Example 42), sodium hydrogen carbonate (176 mg, 2.1 mmol) in dry N,N-dimethylformamide (25 cm3) was added ethyl iodide (0.088 cm3, 1.1 mmol) and the mixture was heated to 0.80° C. for 2 h. Upon cooling, it was diluted with ethyl acetate (100 cm3) and washed with water (5×100 cm3). The organic solution was then dried over sodium sulfate before the solvent was removed in vacuo. The crude material was then passed through a short pad of silica first with dichloromethane (which was discarded) and then with ethyl acetate. The solvent was removed to afford the desired product (194 mg, 51%).

Workup

  1. temperatureUpon cooling
  2. washwashed with water (5×100 cm3)
  3. dry with materialThe organic solution was then dried over sodium sulfate before the solvent
  4. customwas removed in vacuo
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-f2ca22b2c309441f9b76857ca0a85511
Source dataset
uspto-grants-2009_03
Patent number
US07507824B2

Reaction notes

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