Diethyl Ether → HCID 20080506, compound

HRID 1653822Notes

Reaction equation

HRID 1653822 reaction equation
C1(NC2CCCCC2)CCCCC1.[C:14]([CH:16]([CH3:25])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=O)#[N:15].S([O-])(O)(=O)=O.[Na+].C(OCC)C.Cl.[NH2:38][CH:39]([C:49]1[CH:54]=[CH:53][C:52]([Cl:55])=[CH:51][CH:50]=1)[C:40]([C:42]1[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][CH:43]=1)=[O:41]>ClCCl.N1C=CC=CC=1>[Cl:48][C:45]1[CH:44]=[CH:43][C:42]([C:40](=[O:41])[CH:39]([C:49]2[CH:54]=[CH:53][C:52]([Cl:55])=[CH:51][CH:50]=2)[NH:38][C:22](=[O:24])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:16]([C:14]#[N:15])[CH3:25])=[CH:47][CH:46]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 516919Sodium BisulfateHCID 20080512HCID 20080512, compoundHCID 67784761HCID 67784761, compound

Product 1

HCID 20080506HCID 20080506, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

8.2 g of 7-cyanooctanoic acid dicyclohexylamine salt are added to a mixture of 26 cm3 of a molar solution of sodium hydrogen sulphate and 60 cm3 of diethyl ether. The mixture is stirred for 15 minutes at 20° C. and the organic phase is then separated. The latter is dried over magnesium sulphate and filtered and the solvent is evaporated off under reduced pressure. The residue is treated with 13.2 g of thionyl chloride and heated to 50° C. for 3 hours. The mixture is concentrated under reduced pressure. The residual oil is dissolved in 5 cm3 of dichloromethane, and the solution obtained is added to a suspension, stirred and cooled at 5° C. of 7 g of 2-amino-1,2-bis(4-chlorophenyl)ethanone hydrochloride in 25 cm3 of dichloromethane containing 4.4 g of pyridine. After treatment, the product obtained is chromatographed on a column 2.8 cm in diameter containing 140 g of silica gel (50 to 200μ). The column is eluted with 1 liter of diisopropyl ether and then with 2.5 liters of a diisopropyl ether/ethyl acetate (90:10 by volume) mixture, collecting 250 cm3 fractions. The fractions from the last eluent mixture are concentrated to dryness under reduced pressure (0.2 kPa). 7.6 g (80%) of (RS)-1,2-bis(4-chlorophenyl)-2-(7-cyanooctanamido)ethanone are obtained in the form of a yellowish oil, which is used directly in the subsequent reaction.

Workup

  1. customthe organic phase is then separated
  2. dry with materialThe latter is dried over magnesium sulphate
  3. filtrationfiltered
  4. customthe solvent is evaporated off under reduced pressure
  5. additionThe residue is treated with 13.2 g of thionyl chloride
  6. temperatureheated to 50° C. for 3 hours
  7. concentrationThe mixture is concentrated under reduced pressure
  8. dissolutionThe residual oil is dissolved in 5 cm3 of dichloromethane
  9. customthe solution obtained
  10. additionis added to a suspension
  11. stirringstirred
  12. customAfter treatment, the product obtained
  13. customis chromatographed on a column 2.8 cm in diameter
  14. additioncontaining 140 g of silica gel (50 to 200μ)
  15. washThe column is eluted with 1 liter of diisopropyl ether
  16. customwith 2.5 liters of a diisopropyl ether/ethyl acetate (90:10 by volume) mixture, collecting 250 cm3 fractions
  17. concentrationThe fractions from the last eluent mixture are concentrated to dryness under reduced pressure (0.2 kPa)

Sources & evidence

ORD record
ord-b5d8650cf5334fbeb02e3a14d9a39a1b
Source dataset
uspto-grants-1995_04
Patent number
US05403852

Reaction notes

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