Thionyl Chloride → Ethyl 4-(chlorocarbonyl)-1-piperidinecarboxylate

HRID 1585325Notes

Reaction equation

HRID 1585325 reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH2:5]1)(O)=[O:2].S(Cl)([Cl:17])=O>C1(C)C=CC=CC=1>[Cl:17][C:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH2:5]1)=[O:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 66188861-(Ethoxycarbonyl)-4-piperidinecarboxylic Acid

Product 1

HCID 11096122Ethyl 4-(chlorocarbonyl)-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 578.2 g of 4-carboxy-1-ethoxycarbonylpiperidine in 1200 ml of toluene is treated firstly with 1.0 g of N,N-dimethylformnamide and then, at from 68 to 70° C. and within the space of 2 hours, with 369.0 g of thionyl chloride. The mixture is subsequently stirred at 70° C. for a further 30 min, after which the toluene is distilled off in vacuo and the residue is then degassed at RT for approximately 30 min under HV. This results in the title compound in the form of a weakly yellow oil [IR (Film): 2960, 2870, 1790, 1695, 1470, 1435, 1300, 1230, 1130, 960, 765 cm-1 ]. The product distils without decomposition at a m.p. of 96-98° C. (0.08-0.09 Torr).

Workup

  1. customat from 68 to 70° C.
  2. customwithin the space of 2 hours
  3. distillationafter which the toluene is distilled off in vacuo
  4. customthe residue is then degassed at RT for approximately 30 min under HV

Sources & evidence

ORD record
ord-21a3576b5209402aade3fd8b376a7dad
Source dataset
uspto-grants-1999_08
Patent number
US05935976

Reaction notes

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