Iodoethane → HCID 15096762, compound

HRID 345553Notes

Reaction equation

HRID 345553 reaction equation
[OH:1][CH:2]1[C:7]([O:10][CH3:11])([O:8][CH3:9])[CH2:6][CH2:5][N:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:3]1.[H-].[Na+].I[CH2:20][CH3:21]>CN(C)C=O>[CH2:20]([O:1][CH:2]1[C:7]([O:8][CH3:9])([O:10][CH3:11])[CH2:6][CH2:5][N:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:3]1)[CH3:21]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 3019465Ethyl 3-hydroxy-4,4-dimethoxypiperidine-1-carboxylate

Product 1

HCID 15096762HCID 15096762, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
30 °C

Procedure

To a stirred solution of 35 parts of ethyl 3-hydroxy-4,4-dimethoxy-1-piperidinecarboxylate in 144 parts of N,N-dimethylformamide were added portionwise 8.2 parts of a sodium hydride dispersion 50% at about 30° C. After stirring for 1.50 hours at about 30° C., the mixture was cooled to room temperature and 26.5 parts of iodoethane were added dropwise at a temperature below 30° C. Upon completion, stirring was continued for 18 hours at room temperature. The reaction mixture was poured onto water and the product was extracted with 4-methyl-2-pentanone. The extract was washed with water, dried, filtered and evaporated, yielding 34.1 parts (87%) of ethyl 3-ethoxy-4,4-dimethoxy-1-piperidinecarboxylate as a residue (intermediate 67).

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. stirringUpon completion, stirring
  3. waitwas continued for 18 hours at room temperature
  4. additionThe reaction mixture was poured onto water
  5. extractionthe product was extracted with 4-methyl-2-pentanone
  6. washThe extract was washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-c9158f752942417d902ec940af32554c
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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