Isopropanol ethanol → HCID 178480300, compound

HRID 1876753Notes

Reaction equation

HRID 1876753 reaction equation
CCO.CC(O)C.[CH3:8][N:9]1[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][CH2:17][N:18](C(OCC2C=CC=CC=2)=O)[C:19]([NH:21]C(OCC2C=CC=CC=2)=O)=[NH:20])[CH2:11][CH2:10]1.[H][H]>[Pd].O>[CH3:8][N:9]1[CH2:10][CH2:11][CH:12]([CH2:15][CH2:16][CH2:17][NH:18][C:19]([NH2:21])=[NH:20])[CH2:13][CH2:14]1

Participants

6

Reactant 3

HCID 22179027Isopropanol ethanolHCID 140545984HCID 140545984, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178480300HCID 178480300, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A 13 gal (50 liter) Hastelloy pressure reactor equipped with a mechanical agitator, cooling/heating jacket, and addition lines was charged with a solution of 95/5 EtOH/IPA (27.00 kg) and N-[3-(1-methylpiperidin-4-yl)-propyl]-N,N′-di-Cbz-guanidine (7.28 kg, 14.97 mol). To the resultant solution, under nitrogen, was then added 10% Pd/C (50% wet, 0.50 kg). The reactor was sealed and sequentially placed under vacuum, nitrogen and vacuum to displace any air in the system. The reaction was stirred at 1000 RPM and 300-350 PSI of hydrogen while keeping the temperature below 35° C. using cooling water on the jacket. The reaction ceased to be exothermic after approximately 1.5 hours and was stirred for an additional hour at 300-350 PSI. The resultant slurry was filtered over Celite® to yield a solution containing the title compound. The solution was stored at 5° C. and used in the next step without further isolation or purification.

Workup

  1. customA 13 gal (50 liter) Hastelloy pressure reactor equipped with a mechanical agitator
  2. temperaturecooling/heating
  3. additionjacket, and addition lines
  4. customThe reactor was sealed
  5. customthe temperature below 35° C.
  6. filtrationThe resultant slurry was filtered over Celite®
  7. customto yield a solution

Sources & evidence

ORD record
ord-ca1d73f87f1a46c8922d7b5b2887d47e
Source dataset
uspto-grants-2012_11
Patent number
US08309720B2

Reaction notes

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