Diethyl Ether → HCID 86734318, compound

HRID 1448343Notes

Reaction equation

HRID 1448343 reaction equation
[OH:1][CH:2]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:3][N:4]1[CH2:9][CH2:8][C:7]([N:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14](=[O:17])[CH2:15][CH3:16])([CH2:10][O:11][CH3:12])[CH2:6][CH2:5]1.O(CC)CC.[C:35](Cl)(=[O:38])[CH2:36][CH3:37]>C(N(CC)CC)C>[CH3:12][O:11][CH2:10][C:7]1([N:13]([C:14](=[O:17])[CH2:15][CH3:16])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:8][CH2:9][N:4]([CH2:3][CH:2]([O:1][C:35](=[O:38])[CH2:36][CH3:37])[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 62324Propionyl chlorideHCID 12298103HCID 12298103, compound

Product 1

HCID 86734318HCID 86734318, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 8.4 parts of N-[1-(2-hydroxy-2-phenylethyl)-4-(methoxymethyl)-4-piperidinyl]-N-phenylpropanamide in 52.5 parts of 1,1'-oxybisethane are added 2.15 parts of propanoyl chloride and 3.8 parts of N,N-diethylethanamine. The whole is stirred for 5 hours at reflux. The reaction mixture is cooled to room temperature, poured onto water and the layers are separated. The organic phase is washed with water, dried, filtered and evaporated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 7% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The oily residue is converted into the ethanedioate salt in 2-propanol. The solvent is evaporated. The oily residue solidifies on triturating in boiling 4-methyl-2-pentanone. The salt is filtered off and crystallized from 2-propanol. The product is filtered off and dried, yielding 4.6 parts (36.8%) of [2-{4-(methoxymethyl)-4-[(1-oxopropyl)phenylamino]-1-piperidinyl}-1-phenylethyl]propanoate sesquiethanedioate; mp. 171.2° C.

Workup

  1. temperatureat reflux
  2. additionpoured onto water
  3. customthe layers are separated
  4. washThe organic phase is washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe oily residue is purified by column-chromatography over silica gel using
  9. additiona mixture of trichloromethane and 7% of methanol as eluent
  10. customThe pure fractions are collected
  11. customthe eluent is evaporated
  12. customThe solvent is evaporated
  13. customon triturating
  14. filtrationThe salt is filtered off
  15. customcrystallized from 2-propanol
  16. filtrationThe product is filtered off
  17. customdried

Sources & evidence

ORD record
ord-3319518dd9264ca094c7c4fffff7067a
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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