Acetic Acid → HCID 10130805, compound

HRID 2050789Notes

Reaction equation

HRID 2050789 reaction equation
[N:1]1([CH2:6][CH2:7][NH2:8])[CH:5]=[CH:4][CH:3]=[CH:2]1.O=[C:10]1[CH2:15][CH2:14][CH2:13][CH:12]([CH2:16][C:17](OC)=[O:18])[CH2:11]1.O.C(O)(=O)C>C1(C)C=CC=CC=1>[CH:4]1[CH:3]=[CH:2][N:1]2[CH2:6][CH2:7][N:8]3[C:17](=[O:18])[CH2:16][CH:12]4[CH2:13][C:14]3([CH2:15][CH2:10][CH2:11]4)[C:5]=12

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 566095Methyl 2-(3-oxocyclohexyl)acetateHCID 27638162-(1H-pyrrol-1-yl)-1-ethanamine

Product 1

HCID 10130805HCID 10130805, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1.3 g of 2-(1-pyrrolyl)-ethylamine, 2.0 g of methyl 3-oxocyclohexylacetate in 150 ml toluene is stirred and refluxed overnight using a Dean Stark water separator. The reaction is cooled and 7 ml glacial acetic acid is added. The solution is stirred and refluxed as before for 6 hours, cooled and the organic solvents are evaporated under reduced pressure. The residue is dissolved in ether and washed with ice cold 1N aqueous sodium hydroxide. The organic layer is separated, dried over magnesium sulfate, and filtered. The ether solution is evaporated under reduced pressure and the residue is crystallized from ether to give 5,6,10,11,12,13-hexahydro-10,13a-methano-13aH-pyrrolo[2',1':3,4]pyrazino[1,2-a]azocin-8(9H)-one, m.p. 130°-132°, the compound of formula II wherein R, R1R2 and R3 represent hydrogen.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction is cooled
  3. temperaturerefluxed as before for 6 hours
  4. temperaturecooled
  5. customthe organic solvents are evaporated under reduced pressure
  6. dissolutionThe residue is dissolved in ether
  7. washwashed with ice cold 1N aqueous sodium hydroxide
  8. customThe organic layer is separated
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customThe ether solution is evaporated under reduced pressure
  12. customthe residue is crystallized from ether

Sources & evidence

ORD record
ord-b33fc03a635a408aa1588289bf0b2582
Source dataset
uspto-grants-1991_05
Patent number
US05015645

Reaction notes

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