HCID 140545984, compound → HCID 178480300, compound

HRID 1876755Notes

Reaction equation

HRID 1876755 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][CH2:10][N:11](C(OCC2C=CC=CC=2)=O)[C:12]([NH:14]C(OCC2C=CC=CC=2)=O)=[NH:13])[CH2:4][CH2:3]1.[H][H]>[Pd].C(O)C>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([CH2:8][CH2:9][CH2:10][NH:11][C:12]([NH2:14])=[NH:13])[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 140545984HCID 140545984, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178480300HCID 178480300, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a 1-L round bottom flask were added N-[3-(1-methyl-piperidin-4-yl)-propyl]-N,N′-di-cbz-guanidine (140.6 g, 0.301 moles) and ethanol (500 mL, 200 proof). The flask was equipped with a heating mantle and warmed to 50° C. Once a yellow homogeneous solution was obtained, the heating mantle was exchanged for an ice bath and the mixture cooled to an internal temperature of 10° C. The resultant cold mixture was transferred to a 2.25 liter Parr bottle equipped with a thermocouple probe, and 10% Pd on Carbon (10 wt. %) in one portion. The bottle was charged with H2(g) (60 psi). The Parr bottle was kept pressurized with hydrogen gas for 15 minutes, then evacuated, re-pressurized with H2(g) (60 psi) and allowed to shake for an additional hour. The catalyst was removed by filtration (Zap-Cap) and washed with ethanol (300 ml, 200 proof). The solvent was removed under pressure to yield the title compound.

Workup

  1. customThe flask was equipped with a heating mantle and
  2. customOnce a yellow homogeneous solution was obtained
  3. customthe heating mantle was exchanged for an ice bath
  4. temperaturethe mixture cooled to an internal temperature of 10° C
  5. additionThe bottle was charged with H2(g) (60 psi)
  6. customevacuated, re-pressurized with H2(g) (60 psi)
  7. waitto shake for an additional hour
  8. customThe catalyst was removed by filtration (Zap-Cap)
  9. washwashed with ethanol (300 ml, 200 proof)
  10. customThe solvent was removed under pressure

Sources & evidence

ORD record
ord-5a18c32bf6874a6fb5f189426176136a
Source dataset
uspto-grants-2012_11
Patent number
US08309720B2

Reaction notes

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