Dimethylformamide → HCID 18461157, compound

HRID 2303383Notes

Reaction equation

HRID 2303383 reaction equation
[ClH:1].Cl[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[C:11]([O-:14])([O-])=[O:12].[Cs+].[Cs+].CN([CH:20]=[O:21])C>>[N:5]1([CH2:4][CH2:3][O:21][C:20]2[CH:10]=[CH:9][C:8]([C:11]([OH:14])=[O:12])=[CH:7][C:6]=2[Cl:1])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochloride

Product 1

HCID 18461157HCID 18461157, compound

Conditions

Temperature
0 °C

Procedure

7.1 g (35.4 mmol) of 3-chloro-4-hydroxy ethylbenzoate was dissolved in 250 mL of DMF and 13.1 g (71 mmol) of 1-(2-chloroethyl)piperidine hydrochloride and 52 g (160 mmol) of Cs2CO3 was added. The reaction mixture was heated to reflux for four hours. The reaction was allowed to cool and evaporated to dryness. The residue was dissolved in 80 mL of MeOH and 40 mL of 1 N NaOH was added. The reaction mixture was heated to reflux for two hours and cooled to 0° C. The reaction mixture was acidified with 5 N HCl and placed at −20° C. for sixteen hours. The product crystallized out and was filtered off. This yielded 26 g of the title compound as a white powder.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for four hours
  3. temperatureto cool
  4. customevaporated to dryness
  5. dissolutionThe residue was dissolved in 80 mL of MeOH
  6. addition40 mL of 1 N NaOH was added
  7. temperatureThe reaction mixture was heated
  8. temperatureto reflux for two hours
  9. waitplaced at −20° C. for sixteen hours
  10. customThe product crystallized out
  11. filtrationwas filtered off

Sources & evidence

ORD record
ord-4f173aea962046588c08e79d52973ad5
Source dataset
uspto-grants-2002_08
Patent number
US06432982B1

Reaction notes

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