Ethyl Bromide → HCID 12298226, compound

HRID 1973796Notes

Reaction equation

HRID 1973796 reaction equation
[CH2:1]([Mg]Br)[CH3:2].BrCC.[Mg].O=C1[O:14][C:13](=O)[C:12]2([CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16]2)[N:11]1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[Cl-].[NH4+]>O1CCCC1>[O:14]=[C:13]([C:12]1([NH:11][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16]1)[CH2:1][CH3:2]

Participants

7

Reactant 5

HCID 6332Ethyl BromideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 12298225HCID 12298225, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 12298226HCID 12298226, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A Grignard-complex, ethyl magnesium bromide, is prepared in the conventional manner, starting from 10.57 parts of 1-bromoethane and 2.14 parts of magnesium in 27 parts of dry tetrahydrofuran. This complex is added dropwise to a warm suspension of 25.7 parts of ethyl 2,4-dioxo-1-phenyl-3-oxa-1,8-diazaspiro[4,5]decane-8-carboxylate in 213 parts of dry tetrahydrofuran: exothermic reaction. Upon completion, stirring is continued for 1 hour at room temperature. After cooling, the reaction mixture is decomposed by dropwise addition of an ammonium chloride solution. The layers are separated and the aqueous phase is extracted with 1,1'-oxybisethane. The combined organic phases are washed with water, dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 3% of methanol as eluent. The pure fractions are collected and the eluent is evaporated, yielding ethyl 4-(1-oxopropyl)-4-(phenylamino)-1-piperidinecarboxylate as a residue.

Workup

  1. customexothermic reaction
  2. temperatureAfter cooling
  3. customThe layers are separated
  4. extractionthe aqueous phase is extracted with 1,1'-oxybisethane
  5. washThe combined organic phases are washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is purified by column-chromatography over silica gel using
  10. additiona mixture of trichloromethane and 3% of methanol as eluent
  11. customThe pure fractions are collected
  12. customthe eluent is evaporated

Sources & evidence

ORD record
ord-64fc59235f384d409c29a5a4cdbc4ebc
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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