1,2-Dimethoxyethane → HCID 18384010, compound

HRID 2163276Notes

Reaction equation

HRID 2163276 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[C:7]([N+:17]([O-])=O)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(COC)OC.[H][H]>[Pd].CO>[NH2:17][C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=[CH:9][C:8]=1[N:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1

Participants

6

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 18384073HCID 18384073, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18384010HCID 18384010, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-(4-tert-Butyl-2-nitrophenyl)morpholine (15 g.; 57 mmoles) was dissolved in a mixture of 150 ml. of monoglyme and 150 ml. of methanol. The mixture was then hydrogenated in the presence of 1.4 g. of Pd on carbon catalyst (10%) with an initial pressure of 39 p.s.i. hydrogen. After 3 hours, the resultant mixture was filtered to remove the catalyst and the filtrate evaporated to dryness to give the product (13 g.; 97.8% yield) as tan crystals, m.p. 165°-166° C.

Workup

  1. filtrationthe resultant mixture was filtered
  2. customto remove the catalyst
  3. customthe filtrate evaporated to dryness
  4. customto give the product (13 g.; 97.8% yield) as tan crystals, m.p. 165°-166° C.

Sources & evidence

ORD record
ord-1efde72904934029a3a7f14e19f47dc9
Source dataset
uspto-grants-1979_01
Patent number
US04133673

Reaction notes

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