Triethylamine → HCID 14013752, compound

HRID 1763114Notes

Reaction equation

HRID 1763114 reaction equation
Cl[C:2]([F:27])([F:26])[C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]([O:18][CH:19]([CH3:21])[CH3:20])[C:4]=1[C:22]([O:24][CH3:25])=[O:23].C(N(CC)CC)C.[H][H]>C(O)C.[Pd]>[F:27][CH:2]([F:26])[C:3]1[N:8]=[C:7]([C:9]([F:12])([F:10])[F:11])[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]([O:18][CH:19]([CH3:21])[CH3:20])[C:4]=1[C:22]([O:24][CH3:25])=[O:23]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 14013750HCID 14013750, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14013752HCID 14013752, compoundYield 90.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3.0 g (0.007 mol) of product of Example 12, 0.72 g (0.007 mol) of triethylamine and 0.36 g of Pd/C (10%) in 30 ml of ethanol was hydrogenated with 501 kPa hydrogen pressure at 50° C. for 1 hour and filtered. The filtrate was concentrated, the residue dissolved in ether, washed with 3.7% aqueous HCl, dried (MgSO4) and concentrated in vacuo to 2.74 g of a brown oil. This oil was kugelrohr distilled at 67 Pa, pot temperature 90° C., to give 2.45 g (90.8%) of product as a yellow solid; mp 29°-31° C.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. dissolutionthe residue dissolved in ether
  4. washwashed with 3.7% aqueous HCl
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo to 2.74 g of a brown oil
  7. distillationThis oil was kugelrohr distilled at 67 Pa, pot temperature 90° C.

Sources & evidence

ORD record
ord-3fae058433f24894902988cc055e5979
Source dataset
uspto-grants-1989_05
Patent number
US04835279

Reaction notes

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