2-Bromopropane → 1-Methylethyl 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylate

HRID 1448285Notes

Reaction equation

HRID 1448285 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].CN(C)P(=O)(N(C)C)N(C)C.Br[CH:38]([CH3:40])[CH3:39]>O>[C:1]1([NH:7][C:8]2([C:22]([O:24][CH:38]([CH3:40])[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

6

Reactant 4

HCID 63582-Bromopropane2×HCID 12679HexamethylphosphoramideHCID 6162334-Piperidinecarboxylic acid, 4-(phenylamino)-1-(2-phenylethyl)-HCID 5360545Sodium

Product 1

HCID 122981491-Methylethyl 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 10.4 parts of 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylic acid, sodium salt and 75 parts of hexamethylphosphoric triamide is stirred and heated at 110° C. for a while. It is cooled to 20° C. and 3.7 parts of 2-bromopropane are added dropwise. After stirring for 4 hours, another 0.37 parts of 2-bromopropane is added dropwise. Upon completion, stirring is continued over week-end at room temperature. The reaction mixture is poured onto 150 parts of water and the product is extracted with methylbenzene. The extract is washed with water, dried, filtered and evaporated. The oily residue is dissolved in 1,1'-oxybisethane. The solution is stirred with activated charcoal. The latter is filtered off and the filtrate is evaporated. The oily residue is crystallized from hexane. The product is filtered off and recrystallized from hexane, yielding 1-methylethyl 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylate; mp. 78.5° C.

Workup

  1. temperatureIt is cooled to 20° C.
  2. stirringAfter stirring for 4 hours
  3. stirringUpon completion, stirring
  4. waitis continued over week-end at room temperature
  5. extractionthe product is extracted with methylbenzene
  6. washThe extract is washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. dissolutionThe oily residue is dissolved in 1,1'-oxybisethane
  11. stirringThe solution is stirred with activated charcoal
  12. filtrationThe latter is filtered off
  13. customthe filtrate is evaporated
  14. customThe oily residue is crystallized from hexane
  15. filtrationThe product is filtered off
  16. customrecrystallized from hexane

Sources & evidence

ORD record
ord-c9760db79b1b49c7bf6526843a6d0e75
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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