Diethyl Ether → HCID 88766566, compound

HRID 1389991Notes

Reaction equation

HRID 1389991 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])OC1C=CC=C[C:10]=1[O:15][C:16]([CH3:20])([CH3:19])[C:17]#[CH:18].CC[O:25]CC>>[CH3:19][C:16]([CH3:20])([O:15][C:10]([N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)=[O:25])[C:17]#[CH:18]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 4837PiperazineHCID 131712070HCID 131712070, compound

Product 1

HCID 88766566HCID 88766566, compound

Procedure

A stirred mixture of 25.8 g (0.3 mole) of piperazine and 30.6 (0.15 mole) of 1,1-dimethylpropynoxyphenyl carbonate was heated at 90° for 18 hrs. The reaction mixture was cooled and partitioned between excess 5% NaOH solution and 100 ml of CH2Cl2. The layers were separated and the water layer extracted twice more with 100 ml portions of CH2Cl2. The organic extracts were dried (MgSO4), filtered and evaporated to an orange oil. Distillation through a 4-inch Vigreaux column gave 18.3 g (62%) of light yellow oil which solidified on standing, m.p. 35°-8°. The hydrochloride salt prepared in ether and recrystallized from acetonitrile had a m.p. of 193°-4° dec. Calc. for C10H17ClN2O2 (232.71): C, 51.61; H, 7.36; Cl, 15.23; N, 12.04. Found: C, 51.37; H, 7.39; Cl, 15.19; N, 11.92.

Workup

  1. temperaturewas heated at 90° for 18 hrs
  2. temperatureThe reaction mixture was cooled
  3. custompartitioned between excess 5% NaOH solution and 100 ml of CH2Cl2
  4. customThe layers were separated
  5. extractionthe water layer extracted twice more with 100 ml portions of CH2Cl2
  6. dry with materialThe organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated to an orange oil
  9. distillationDistillation through a 4-inch Vigreaux column
  10. customgave 18.3 g (62%) of light yellow oil which
  11. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-0f8c460949a145a0bff3ba89352e849a
Source dataset
uspto-grants-1981_01
Patent number
US04247549

Reaction notes

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