N-Hydroxyphthalimide → HCID 15712604, compound

HRID 1533872Notes

Reaction equation

HRID 1533872 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][CH:14]1[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]1.O[N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.Cl.C(OCC)(=O)C>[CH3:20][N:17]1[CH2:18][CH2:19][CH:14]([O:13][N:22]2[C:23](=[O:32])[C:24]3=[CH:31][CH:30]=[CH:29][CH:28]=[C:25]3[C:26]2=[O:27])[CH2:15][CH2:16]1

Participants

8

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 660484-Piperidinol, 1-methyl-HCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 15712604HCID 15712604, compoundYield 27.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

N-(1-Methyl-4-piperidyloxy)phthalimide may be obtained in the following manner: diethyl azodicarboxylate (53.8 g) is added in the course of 90 minutes at a temperature in the region of 0° C. to a suspension of 4-hydroxy-1-methylpiperidine (30.6 g), N-hydroxyphthalimide (43.7 g) and triphenylphosphine (68.3 g) in tetrahydrofuran (450 cc). The suspension obtained is stirred at a temperature in the region of 20° C. for 18 hours and the reaction mixture is then concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the region of 40° C. The product obtained is taken up with ethyl acetate (500 cc) and the suspension obtained is filtered. The filtrate is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the region of 40° C. The product obtained is redissolved in N aqueous hydrochloric acid solution (500 cc). The suspension obtained is filtered and the filtrate is extracted 3 times with ethyl ether (300 cc in total) and brought to a pH in the range of 10 by adding N aqueous sodium hydroxide solution (500 cc) The crystals which appear are separated by filtration, washed 3 times with distilled water (300 cc in total) and dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the region of 20° C. N-(1-Methyl-4-piperidyloxy)phthalimide (19 g) is thereby obtained in the form of beige crystals, m.p. 90° C.

Workup

  1. customThe suspension obtained
  2. concentrationthe reaction mixture is then concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the region of 40° C
  3. customThe product obtained
  4. customthe suspension obtained
  5. filtrationis filtered
  6. concentrationThe filtrate is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the region of 40° C
  7. customThe product obtained
  8. customThe suspension obtained
  9. filtrationis filtered
  10. extractionthe filtrate is extracted 3 times with ethyl ether (300 cc in total)
  11. additionby adding N aqueous sodium hydroxide solution (500 cc) The crystals which
  12. customappear are separated by filtration
  13. washwashed 3 times with distilled water (300 cc in total)
  14. customdried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the region of 20° C

Sources & evidence

ORD record
ord-94cba300372b4b5b8db2c569b7a50b67
Source dataset
uspto-grants-1992_02
Patent number
US05086051

Reaction notes

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