Dimethylformamide → Ethyl 4-(chlorocarbonyl)-1-piperidinecarboxylate

HRID 1377154Notes

Reaction equation

HRID 1377154 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].CN(C)C=O.S(Cl)([Cl:22])=O>C1(C)C=CC=CC=1>[Cl:22][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

5

Reactant 3

HCID 6228DimethylformamideHCID 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-dimethylformamide 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-ff66d6f0e52c46eaab2028603259ce82
Source dataset
uspto-grants-1997_09
Patent number
US05663200

Reaction notes

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