Morpholine → HCID 14213086, compound

HRID 1722677Notes

Reaction equation

HRID 1722677 reaction equation
[CH3:1][C:2]([CH:10](C(O)=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([N:21]([CH2:24]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])C=CC=CC=1.[NH:43]1[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1>C1(C)C=CC=CC=1>[N:43]1([C:24]([NH:21][CH:10]([C:2]([CH3:1])([CH3:9])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:33])[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 14213083HCID 14213083, compound

Product 1

HCID 14213086HCID 14213086, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl hydrogen (α, α-dimethylbenzyl)malonate (4 g, 0.016 mol) in toluene was added triethylamine (2.33 ml, 0.016 mol) and diphenylphosphoryl azide (4.4 g, 0.016 mol). The reaction mixture was heated at 100° C. for 2.5 h, cooled to 5° C., and treated with 1.4 ml (0.016 mol) of morpholine. After stirring overnight at room temperature, the toluene solution was washed successively with 1N HCl and aqueous sodium bicarbonate solution. The dried organic solution was evaporated to a residue which was purified by column chromatography on silica gel. There was obtained 3.7 g (69%) of product after trituration with hexane, mp 93°-94° C.

Workup

  1. temperaturecooled to 5° C.
  2. washthe toluene solution was washed successively with 1N HCl and aqueous sodium bicarbonate solution
  3. customThe dried organic solution was evaporated to a residue which
  4. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-caa9b9cf9ccb431792541071a0451786
Source dataset
uspto-grants-1989_08
Patent number
US04857507

Reaction notes

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