N-(2-oxiranylmethoxy)phthalimide → HCID 86759178, compound

HRID 1169127Notes

Reaction equation

HRID 1169127 reaction equation
O1CC1CO[N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16].[C:17]1([CH:23]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:24][CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[C:31]1([CH:23]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[O:24][CH:25]2[CH2:30][CH2:29][N:28]([CH2:17][CH:23]([OH:24])[CH2:31][C:15]3[CH:14]=[CH:13][CH:12]=[C:9]4[C:10]([NH:6][C:7](=[O:16])[C:8]=34)=[O:11])[CH2:27][CH2:26]2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 257783N-(2-oxiranylmethoxy)phthalimideHCID 30175844-Benzhydryloxypiperidine

Product 1

HCID 86759178HCID 86759178, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.70 g of potassium phthalimide was dissolved in 20 ml of N,N-dimethylformamide; 2.58 ml of epibromohydrin was added, followed by stirring at room temperature for 15 hours. Ice water was added to the reaction mixture, followed by extraction with ethyl acetate; the extract was washed with saline, dried over magnesium sulfate and concentrated under reduced pressure; ethyl ether was added to the residue; the crystal precipitated was collected to yield 3.7 g of N-(2-oxiranylmethoxy)phthalimide. 0.61 g of N-(2-oxiranylmethoxy)phthalimide and 0.802 g of 4-(diphenylmethoxy)piperidine were dissolved n 10 ml of ethanol, followed by thermal refluxing for 2 hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate. The desired fraction was collected to yield 1.30 g of N-[3-[4-(diphenylmethoxy)piperidino-2-hydroxypropyl]phthalimide as an oily substance. This oily substance was dissolved in 10 ml of ethanol; 0.14 ml of hydrazine monohydrate was added, followed by thermal refluxing for 3 hours. After cooling, the mixture was concentrated under reduced pressure; ethanol was added to the residue; the crystal precipitated was collected, dissolved in 3 ml of a 1 N aqueous solution of sodium hydroxide and 10 ml of water and extracted with ethyl acetate; the extract was washed with saline, dried over sodium sulfate and concentrated under reduced pressure; the crystal obtained was collected to yield 0.76 g of the title compound.

Workup

  1. customrefluxing for 2 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washeluted with ethyl acetate
  4. customThe desired fraction was collected

Sources & evidence

ORD record
ord-cbfdb7b365b84472addd6d8dbbbedb72
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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