Morpholine → HCID 14213086, compound

HRID 1110996Notes

Reaction equation

HRID 1110996 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 mole) in toluene was added triethylamine (2.23 ml, 0.016 mole) and diphenylphosphoryl azide (4.4 g, 0.016 mole). The reaction mixture was heated at 100° C. for 2.5 h, cooled to 5° C., and treated with 1.4 ml (0.016 mole) 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, m.p. 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-9354c718ceb94ff9807616eeae80c6df
Source dataset
uspto-grants-1990_12
Patent number
US04977277

Reaction notes

Loading…