Benzylethanolamine → 4-Benzylmorpholine-2-carbonitrile

HRID 218325Notes

Reaction equation

HRID 218325 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(=C)[C:14]#[N:15].O1CC[CH2:19][CH2:18]1.CC(C)([O-])C.[K+]>C(OCC)C>[CH2:1]([N:8]1[CH2:19][CH2:18][O:11][CH:10]([C:14]#[N:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 4348Benzylethanolamine2×HCID 8028TetrahydrofuranHCID 701982-Chloroacrylonitrile2×HCID 23665647Potassium tert-butoxide

Product 1

HCID 156511954-Benzylmorpholine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of N-benzylethanolamine (intermediate 23, 44.8 ml, 314 mmol) and 2-chloroacrylonitrile (intermediate 24, 25 ml, 314 mmol) was stirred at room temperature for 24 hours. After the mixture was cooled to 0° C., tetrahydrofuran (300 ml) and then potassium tert-butoxide was added to the mixture, and the mixture was stirred at 0° C. for one hour. The mixture was diluted by ethyl ether, and then washed with water and brine and dried over magnesium sulfate. Solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; 5% ethyl acetate in hexane) to afford 4-benzylmorpholine-2-carbonitrile (intermediate 25) as colorless oil.

Workup

  1. temperatureAfter the mixture was cooled to 0° C.
  2. stirringthe mixture was stirred at 0° C. for one hour
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customSolvent was removed under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent; 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-42529f5324bb4c9693c8da923afa18cf
Source dataset
uspto-grants-2012_06
Patent number
US08198437B2

Reaction notes

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