Hydrochloric Acid → HCID 19760902, compound

HRID 1534896Notes

Reaction equation

HRID 1534896 reaction equation
[ClH:1].[NH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:8][C:9]([C:11]1[O:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-:24])=[O:23])=[CH:14][CH:15]=1)=[O:10].[CH2:25]=O>CCOCC.C(O)CCC>[ClH:1].[N+:22]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:13]1[O:12][C:11]([C:9](=[O:10])[CH2:8][CH2:25][N:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)=[CH:15][CH:14]=1)([O-:24])=[O:23]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 712FormaldehydeHCID 8082PiperidineHCID 27558581-[5-(2-Nitro-phenyl)-furan-2-yl]-ethanone

Product 1

HCID 19760902HCID 19760902, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Concentrated HCl (16 ml.) is added to a stirred solution of 17 g. (0.20 mole) of piperidine in 100 ml. of n-butanol. To this solution is added 23 g. (0.10 mole) of 5-(o-nitrophenyl)-2-furyl methyl ketone and 6.0 g. (0.20 mole) of paraformaldehyde. The solution is heated under reflux for 3 hr. and the solvent is removed on a rotary evaporator. The residual semi-solid is partitioned between ether and water, the layers are separated, and the ether layer is dried over MgSO4. The solvent is removed on a rotary evaporator to give a residual oil. The oil is dissolved in anhydrous ether and is treated with ethereal HCl. The solid is collected by filtration and is dissolved in 300 ml. of CH3CN. The solution is concentrated and cooled in ice to give solid which is collected by filtration. Recrystallization from CH3CN and then recrystallization with absolute ethanol-anhydrous ether mixture gives 6.5 g. (28%) of product, m.p. 160°-162°.

Workup

  1. additionTo this solution is added 23 g
  2. temperatureThe solution is heated
  3. temperatureunder reflux for 3 hr
  4. customand the solvent is removed on a rotary evaporator
  5. customThe residual semi-solid is partitioned between ether and water
  6. customthe layers are separated
  7. dry with materialthe ether layer is dried over MgSO4
  8. customThe solvent is removed on a rotary evaporator
  9. customto give a residual oil
  10. filtrationThe solid is collected by filtration
  11. dissolutionis dissolved in 300 ml
  12. concentrationThe solution is concentrated
  13. temperaturecooled in ice
  14. customto give solid which
  15. filtrationis collected by filtration
  16. customRecrystallization from CH3CN
  17. customrecrystallization with absolute ethanol-anhydrous ether mixture
  18. customgives 6.5 g

Sources & evidence

ORD record
ord-e8fc1245a8fa41e5a5eee4adb8b021c6
Source dataset
uspto-grants-1992_02
Patent number
US05091426

Reaction notes

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