Ethyl 4-piperidinecarboxylate → Ethyl 1-(((Ethoxy-(propylthio)phosphinyl)amino)carbonyl)-4-piperidinecarboxylate

HRID 465300Notes

Reaction equation

HRID 465300 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.[P:12](=[O:23])([N:20]=[C:21]=[O:22])([S:16][CH2:17][CH2:18][CH3:19])[O:13][CH2:14][CH3:15]>CCOCC>[CH2:14]([O:13][P:12]([NH:20][C:21]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1)=[O:22])([S:16][CH2:17][CH2:18][CH3:19])=[O:23])[CH3:15]

Participants

4

Reactant 2

HCID 70770Ethyl 4-piperidinecarboxylateHCID 19873995O-ethyl S-propyl phosphoroisocyanatidothioate

Product 1

HCID 15017116Ethyl 1-(((Ethoxy-(propylthio)phosphinyl)amino)carbonyl)-4-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2.36 g of ethyl 4-piperidine-carboxylate in 50 ml of ether at ambient temperature was added dropwise with stirring 3.14 g of O-ethyl S-n-propyl phosphoroisocyanatidothioate. The mixture was allowed to stir overnight and was then concentrated by evaporation under reduced pressure using a rotary evaporator and then a Kugelrohr apparatus at 55° C. and 13 Pascals pressure. The residue, which was the title compound, amounted to 5.2 g (94 percent of theory) and was an amber colored viscous oil having a refractive index at 25° C. of 1.5083.

Workup

  1. concentrationwas then concentrated by evaporation under reduced pressure
  2. customa rotary evaporator
  3. customat 55° C.
  4. customat 25° C.

Sources & evidence

ORD record
ord-ad709f3c9da94e498795a254cf41f9f4
Source dataset
uspto-grants-1992_10
Patent number
US05153184

Reaction notes

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