Ammonium Chloride → HCID 21837536, compound

HRID 1739801Notes

Reaction equation

HRID 1739801 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]3)[C:5]=2[O:4][CH2:3][CH2:2]1.[CH3:18][Mg]Br.[NH4+].[Cl-]>CCOCC>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][C:14]([OH:17])([CH3:18])[CH2:13][CH2:12]3)[C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 22122651HCID 22122651, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 21837536HCID 21837536, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

3.5 g (15 mmol) of 1-(2,3-dihydro[1,4]benzodioxin-5-ylpiperid-4-one are dissolved in 30 ml of ether. The solution is cooled to 0° C. and, while that temperature is maintained, 10 ml of a 3M methylmagnesium bromide solution in ether are added. The whole is stirred for 1 hour at that temperature and then for 1/2 hour at room temperature, hydrolysed by pouring into 100 ml of a saturated aqueous NH4Cl solution, and extracted with 100 ml of ether. The extract is dried and evaporated to yield a residue of 3.3 g, which is purified by flash chromatography on silica (eluant CH2Cl2 /CH3COOC2H5 : 90/10). In that manner, 1.3 g of the expected product are isolated.

Workup

  1. temperatureis maintained
  2. waitfor 1/2 hour at room temperature
  3. extractionextracted with 100 ml of ether
  4. customThe extract is dried
  5. customevaporated
  6. customto yield a residue of 3.3 g, which
  7. customis purified by flash chromatography on silica (eluant CH2Cl2 /CH3COOC2H5 : 90/10)

Sources & evidence

ORD record
ord-edfd72de557c48ce9b0a5d07eb5d661e
Source dataset
uspto-grants-1999_10
Patent number
US05968954

Reaction notes

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