Morpholine → HCID 131720366, compound

HRID 1941130Notes

Reaction equation

HRID 1941130 reaction equation
C(Cl)(=O)C(Cl)=O.C[C:8]1[S:9][C:10]([CH2:24][CH2:25][C:26]([CH3:32])([CH3:31])[CH2:27][C:28]([OH:30])=O)=[C:11](CCCC2C=CC(C)=CC=2)[C:12]=1C.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>C(Cl)(Cl)Cl.CCOCC>[O:36]1[CH2:37][CH2:38][N:33]([C:28]([CH2:27][C:26]([CH3:31])([CH3:32])[CH2:25][CH2:24][C:10]2[S:9][CH:8]=[CH:12][CH:11]=2)=[O:30])[CH2:34][CH2:35]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 65578Oxalyl chlorideHCID 54306391HCID 54306391, compound

Product 1

HCID 131720366HCID 131720366, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

2 g (0.0157 mol) of oxalyl chloride dissolved in 10 ml of CHCl3 are placed in a 100 ml single-necked flask. After having brought the mixture to 0° C. with an ice bath, 3.9 g (0.0105 mol) of 2,3-dimethyl-4-(3-p-methylphenylpropyl)-5-(4-carboxy-3,3-dimethylbutyl)thiophene (see above, paragraph B of the synthesis of the starting materials) are added. The reaction mixture is then stirred at room temperature and subsequently at 50° C. until the evolution of gas has ceased. The solvent is distilled off at a temperature below 50° C. The acid chloride prepared above dissolved in 60 ml of ether, and 1.82 g (0.021 mol) of morpholine dissolved in 60 ml of ether, are simultaneously poured into a 500 ml three-necked flask while stirring. The morpholinium hydrochloride precipitates instantaneously. After one hour's stirring, the solid is removed by filtration. The filtrate is washed with water, dried over MgSO4, rendered colourless with carbon black and concentrated to dryness. The crude product obtained is purified by chromatography on silica (eluant: CH2Cl2 /CH3COOC2H5 -95/5, then CH2Cl2 /CH3OH-98/2). 3.31 g of 2,3-dimethyl-4-3-p-methylphenylpropyl)-5-(4-morpholinocarbonyl-3,3-dimethylbutyl)thiophene are obtained in the form of a colourless oil, yield: 72%.

Workup

  1. customare placed in a 100 ml single-necked flask
  2. customto 0° C.
  3. customparagraph B of the synthesis of the starting materials)
  4. additionare added
  5. distillationThe solvent is distilled off at a temperature below 50° C
  6. customThe acid chloride prepared
  7. additionare simultaneously poured into a 500 ml three-necked flask
  8. stirringwhile stirring
  9. customThe morpholinium hydrochloride precipitates instantaneously
  10. stirringAfter one hour's stirring
  11. customthe solid is removed by filtration
  12. washThe filtrate is washed with water
  13. dry with materialdried over MgSO4
  14. concentrationconcentrated to dryness
  15. customThe crude product obtained
  16. customis purified by chromatography on silica (eluant

Sources & evidence

ORD record
ord-5a2d832040e64620b070232ca43afbc4
Source dataset
uspto-grants-1997_12
Patent number
US05703074

Reaction notes

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