Diethyl Ether → HCID 20080542, compound

HRID 1653825Notes

Reaction equation

HRID 1653825 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:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:40]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:41]>ClCCl.N1C=CC=CC=1>[C:42]1([C:40](=[O:41])[CH:39]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=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:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 516919Sodium BisulfateHCID 12306985885-75-6HCID 67784761HCID 67784761, compound

Product 1

HCID 20080542HCID 20080542, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

9 g of 7-cyanooctanoic acid dicyclohexylamine salt is added to a mixture of 28 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 14.8 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 6 cm3 of dichloromethane, and the solution obtained is added to a suspension, stirred and cooled to 5° C. of 6 g of 2-amino-1,2-diphenylethanone hydrochloride in 30 cm3 of dichloromethane containing 4.8 g of pyridine. After treatment, the product obtained is chromatographed on a column 2 cm in diameter containing 48 g of silica gel (50 to 200μ). The column is eluted, collecting 100 cm3 fractions, with 1.2 liters of a diisopropyl ether/ethyl acetate (80:20 by volume) mixture. The fractions emerging at between 0.3 and 1.2 liters are concentrated under reduced pressure (0.2 kPa). 5.9 g (67%) of (RS) -1,2-diphenyl-2-(7-cyanooctanamido)ethanone are obtained in the form of an 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 14.8 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 6 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 cm in diameter
  14. additioncontaining 48 g of silica gel (50 to 200μ)
  15. washThe column is eluted
  16. customcollecting 100 cm3 fractions
  17. concentrationare concentrated under reduced pressure (0.2 kPa)

Sources & evidence

ORD record
ord-b1311078705748999e4621dc49181987
Source dataset
uspto-grants-1995_04
Patent number
US05403852

Reaction notes

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