Hexane → HCID 178420463, compound

HRID 1492176Notes

Reaction equation

HRID 1492176 reaction equation
[C:1]1(=O)[NH:6][CH2:5][CH2:4][CH2:3][CH2:2]1.P(Cl)(Cl)(Cl)=O.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.CCCCCC>C1C=CC=CC=1>[NH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][C:1]1=[N:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 8058HexaneHCID 126652-PiperidoneHCID 24813Phosphorus oxychlorideHCID 7357562-Morpholinoaniline

Product 1

HCID 178420463HCID 178420463, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
65 °C

Procedure

A solution of delta-valerolactam (24 g) in dry benzene (100 ml) was cooled to 10° C. in ice-water and treated with freshly distilled phosphorus oxychloride (22.2 ml) under nitrogen over a period of 10-15 minutes. The initial white solid formed changed to a clear yellow oil over 3 hours. A solution of 4-(2-aminophenyl)morpholine (36 g) in dry benzene (150 ml) was added and the mixture heated at 65° C. with stirring for 32 hours. The benzene layer was decanted, the oil washed twice with benzene (2×40 ml), ether (100 ml) was added and the mixture cooled in ice treated with 10% aqueous sodium hydroxide solution to alkaline pH, with stirring. The aqueous layer was extracted with ether (2×100 ml) and the combined ether extracts washed with water, brine and dried. The solution was filtered and the solvent removed to give a thick oil which solidified on trituration with hexane. The crude solid was crystallised from hot hexane to yield 4-[ 2-(2-piperidinylideneamino)phenyl]morpholine (m.p. 89°-90° C.).

Workup

  1. customThe initial white solid formed
  2. customThe benzene layer was decanted
  3. washthe oil washed twice with benzene (2×40 ml), ether (100 ml)
  4. additionwas added
  5. temperaturethe mixture cooled in ice
  6. additiontreated with 10% aqueous sodium hydroxide solution
  7. stirringwith stirring
  8. extractionThe aqueous layer was extracted with ether (2×100 ml)
  9. washthe combined ether extracts washed with water, brine
  10. customdried
  11. filtrationThe solution was filtered
  12. customthe solvent removed
  13. customto give a thick oil which
  14. customThe crude solid was crystallised from hot hexane

Sources & evidence

ORD record
ord-da4fdda5a5e34fc0819f4787ac178f1d
Source dataset
uspto-grants-1994_12
Patent number
US05373008

Reaction notes

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