1-Morpholinocyclopentene → 4-Cyclopentylmorpholine

HRID 325759

Reaction equation

HRID 325759 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH2:11][CH2:10][CH2:9][CH:8]=2)[CH2:3][CH2:2]1.P(O)(O)O>>[CH:7]1([N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

3

Reactant 2

HCID 702941-MorpholinocyclopenteneHCID 107909Phosphorous acid

Product 1

HCID 134280244-CyclopentylmorpholineYield 72%

Procedure

1-Morpholinocyclopentene (30 g; 0.2 mole) was mixed with phosphorous acid (16.4 g; 0.2 mole) and heated with stirring. As the temperature reached 70° an exothermic process took place taking the internal temperature to 105°. The viscosity of the reaction mixture increased as the reaction proceeded. After maintaining at 100°-105° for 30 mins. the reaction mixture was diluted and basified. Extraction with chloroform yielded N-cyclopentylmorpholine (72%). The product was characterized by 13C and 1H nmr spectra. ##STR16##

Workup

  1. temperatureheated
  2. customreached 70°
  3. customto 105°
  4. temperatureThe viscosity of the reaction mixture increased as the reaction
  5. temperatureAfter maintaining at 100°-105° for 30 mins
  6. additionthe reaction mixture was diluted
  7. extractionExtraction with chloroform

Sources & evidence

ORD record
ord-c932030578294bf5a0da6437b3e8f9b9
Source dataset
uspto-grants-1984_04
Patent number
US04442286

Linked notes

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