Water → Diisopropyl Ether

HRID 1973790Notes

Reaction equation

HRID 1973790 reaction equation
[C:1]1([NH:7][C:8]2([C:22]([OH:24])=[O:23])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].[CH3:26]N(C)P(=O)(N(C)C)N(C)C.I[CH2:38][CH3:39].[OH2:40]>>[O:40]([CH:38]([CH3:39])[CH3:26])[CH:1]([CH3:6])[CH3:2].[C:1]1([NH:7][C:8]2([C:22]([O:24][CH2:38][CH3:39])=[O:23])[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:12][CH2:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6340IodoethaneHCID 12679HexamethylphosphoramideHCID 6162334-Piperidinecarboxylic acid, 4-(phenylamino)-1-(2-phenylethyl)-HCID 5360545Sodium

Product 2

HCID 7914Diisopropyl EtherHCID 12298147Ethyl 1-phenethyl-4-(phenylamino)piperidine-4-carboxylate

Procedure

To a stirred suspension of 58.5 parts of 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylic acid, sodium salt in 300 parts of hexamethylphosphoric triamide are added dropwise 29.2 parts of iodoethane at room temperature (slightly exothermic reaction: the temperature rises to 34° C). Upon completion, stirring is continued at room temperature for 48 hours. The reaction mixture is poured onto 1000 parts of water and the product is extracted with methylbenzene. The extract is washed with water, dried, filtered and evaporated. The residue is crystallized twice: first from petroleumether and then from 35 parts of 2,2'-oxybispropane, yielding 45.2 parts of ethyl 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylate; mp. 65.4° C.

Workup

  1. customslightly exothermic reaction
  2. customrises to 34° C
  3. extractionthe product is extracted with methylbenzene
  4. washThe extract is washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is crystallized twice

Sources & evidence

ORD record
ord-4640b12f62ca46bab597827142b9c2d9
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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