Methyl Isobutyl Ketone → HCID 131729196, compound

HRID 409615Notes

Reaction equation

HRID 409615 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]([CH:11]([O:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[O:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[O:10])[CH2:4][CH2:3]1.[CH2:28]([C:32]([CH3:34])=[O:33])[CH:29]([CH3:31])[CH3:30]>[Pd]>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]([CH:11]([O:20][C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)[O:12][C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[O:10])[CH2:4][CH2:3]1.[CH3:30][CH:29]([CH2:28][C:32]([CH3:34])=[O:33])[CH3:31]

Participants

4

Reactant 2

HCID 7909Methyl Isobutyl KetoneHCID 31060Lifibrate

Product 1

HCID 131729196HCID 131729196, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
90 °C

Procedure

An amount of 20.5 grams 10% Pd/C catalyst (50% wet) (3 wt % based on MPCA+MIBK) was charged to a one liter SS reactor, followed by 149.8 grams (0.48 m) MPCA dissolved in 165.75 grams (1.66 m) methyl isobutyl ketone (MIBK). The reactor was purged three times and leak checked with N2, then purged three times and leak checked with H2. The reaction mix was heated to 90° C. and charged with 100 psi H2 connected to a H2 ballast tank. The reaction was allowed to proceed 22 hours then the H2 pressure raised to 800 psi and allowed to proceed an additional 5 hours. The crude reaction mixture was then filtered through 0.5 μm filter using a pressure filter apparatus, followed by removal of excess MIBK by vacuum evaporation. The GC analysis shown below in Table I indicated alkylation had occurred, and the amine titration showed 5.58 meg/g (AEW 179.2 g/eqv). The AEW indicates an alkylation level of (67/86) 0.78 per nitrogen.

Workup

  1. customThe reactor was purged three times
  2. custompurged three times
  3. additionThe reaction mix
  4. additioncharged with 100 psi H2
  5. temperaturethe H2 pressure raised to 800 psi
  6. waitto proceed an additional 5 hours
  7. customThe crude reaction mixture
  8. filtrationwas then filtered through 0.5 μm
  9. filtrationfilter
  10. filtrationfilter apparatus
  11. customfollowed by removal of excess MIBK by vacuum evaporation

Sources & evidence

ORD record
ord-224d51e815e0433ab45993e1f0d40558
Source dataset
uspto-grants-2014_06
Patent number
US08759470B2

Reaction notes

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