4-Toluenesulfonyl chloride → HCID 21255131, compound

HRID 636566Notes

Reaction equation

HRID 636566 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][CH3:3].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(N(CC)CC)C.[C:25]([N:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]1C(O)=O)(=O)[C:26]1[CH:31]=[CH:30][CH:29]=[N:28][CH:27]=1>ClCCl.C(OCC)(=O)C>[N:28]1[CH:29]=[CH:30][CH:31]=[C:26]([C:25]2[N:33]3[C:34]([CH2:35][CH2:36][CH2:37][CH2:38]3)=[C:2]([C:1]([O:5][CH3:6])=[O:4])[CH:3]=2)[CH:27]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine3×HCID 11124Methyl propionateHCID 162282641-(Pyridine-3-carbonyl)piperidine-2-carboxylic acid2×

Product 1

HCID 21255131HCID 21255131, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1.33 g of methyl propionate are added to a solution of 3.01 g of para-toluenesulphonyl chloride in 17 cm3 of dichloromethane. A solution of the triethylamine salt of N-nicotinoylpiperidine-2-carboxylic acid in 17 cm3 of dichloromethane, prepared from 3.38 g of N-nicotinoylpiperidine-2-carboxylic acid and 2 cm3 of triethylamine, is added slowly with stirring. 2.3 cm3 of triethylamine are then added slowly. The mixture is kept at 25° C. with stirring overnight at ambient temperature. The reaction mixture is concentrated at reduced pressure (2.7 kPa) at a temperature close to 40° C. A residue is thus obtained, which is taken up in 25 cm3 of ethyl acetate and filtered. The filtrate is concentrated at reduced pressure (2.7 kPa) at a temperature close to 40° C. This residue is taken up again in 25 cm3 of ethyl acetate and filtered and then the filtrate is concentrated to dryness. The residue is crystallized from 15 cm3 of ethyl ether. The solid is filtered off and dried in air. 1.1 g of methyl 3-(3-pyridyl)-5,6,7,8-tetrahydroindolizine-1-carboxylate are thus obtained in the form of a cream solid melting at 122° C., containing approximately 5% of methyl 3-(3-pyridyl)-5,6,7,8-tetrahydroindolizine-2-carboxylate.

Workup

  1. additionis added slowly
  2. customis kept at 25° C.
  3. stirringwith stirring overnight at ambient temperature
  4. concentrationThe reaction mixture is concentrated at reduced pressure (2.7 kPa) at a temperature
  5. customclose to 40° C
  6. customA residue is thus obtained
  7. filtrationfiltered
  8. concentrationThe filtrate is concentrated at reduced pressure (2.7 kPa) at a temperature
  9. customclose to 40° C
  10. filtrationfiltered
  11. concentrationthe filtrate is concentrated to dryness
  12. customThe residue is crystallized from 15 cm3 of ethyl ether
  13. filtrationThe solid is filtered off
  14. customdried in air

Sources & evidence

ORD record
ord-339f87fb6936489e84a235cd2497eb7d
Source dataset
uspto-grants-2001_02
Patent number
US06194426B1

Reaction notes

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