6-Nitroveratraldehyde → 6-Nitroveratrylidene-2-aminomethyltetrahydropyran

HRID 436452Notes

Reaction equation

HRID 436452 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][O:4]1.[N+:9]([C:12]1[C:17]([CH:18]=O)=[CH:16][C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=1)([O-:11])=[O:10]>C(O)C>[N+:9]([C:12]1[C:17]([CH:18]=[C:8]2[CH2:7][CH2:6][CH2:5][O:4][CH:3]2[CH2:2][NH2:1])=[CH:16][C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=1)([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 885056-NitroveratraldehydeHCID 97924(Tetrahydro-2H-pyran-2-ylmethyl)amine

Product 1

HCID 542260806-Nitroveratrylidene-2-aminomethyltetrahydropyran

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 2-aminomethyltetrahydropyran (51 g, 0.44 mole) and ethanol (50 ml) was slowly added to a heated suspension of 6-nitroveratraldehyde (84 g, 0.4 mole) and ethanol (600 ml). The resulting solution was refluxed for 1.5 hrs and cooled overnight. The solution was concentrated to dryness and the oil was disolved in chloroform and washed with water. The chloroform extract was concentrated leaving a dark oil which crystallized upon standing. The solid was suspended in hexane and filtered (117 g. 95%), m.p. 89°-96°.

Workup

  1. temperatureThe resulting solution was refluxed for 1.5 hrs
  2. temperaturecooled overnight
  3. concentrationThe solution was concentrated to dryness
  4. washwashed with water
  5. extractionThe chloroform extract
  6. concentrationwas concentrated
  7. customleaving a dark oil which
  8. customcrystallized
  9. filtrationfiltered (117 g. 95%), m.p. 89°-96°

Sources & evidence

ORD record
ord-6a848c78ed574a8b88d1cdd5376757d9
Source dataset
uspto-grants-1977_02
Patent number
US04009177

Reaction notes

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