Hydrochloric Acid → HCID 87477169, compound

HRID 2387242Notes

Reaction equation

HRID 2387242 reaction equation
[F:1][C@@H:2]1[CH2:6][CH2:5][C@H:4]([N:7]2[CH2:12][CH2:11][N:10](C(OCC3C=CC=CC=3)=O)[CH2:9][C:8]2=[O:23])[CH2:3]1.[ClH:24]>CO.[Pd]>[Cl-:24].[F:1][CH:2]1[CH2:6][CH2:5][CH:4]([N:7]2[CH2:12][CH2:11][NH2+:10][CH2:9][C:8]2=[O:23])[CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 131729948HCID 131729948, compound

Product 1

HCID 87477169HCID 87477169, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

A stirred solution of NN2 (1 eq) and Pd/C (10% w/w, 0.3 eq) in MeOH (0.1 M) was hydrogenated under an H2 in presence of 6 M HCl (1 eq). After 16 h the catalyst was filtered off and volatiles were removed under reduced pressure. The resulting crude was again dissolved in MeOH (0.1 M) and new Pd/C catalyst (10% w/w, 0.3 eq) and 6 M HCl (1 eq) was added, and the reaction was hydrogenated for further 2 h. Then the catalyst was filtered off and volatiles evaporated, the resulting crude was used as such in the next step. MS (ES) C9H16FN2O requires: 187 found: 188 (M+H)+.

Workup

  1. filtrationAfter 16 h the catalyst was filtered off
  2. customvolatiles were removed under reduced pressure
  3. dissolutionThe resulting crude was again dissolved in MeOH (0.1 M)
  4. filtrationThen the catalyst was filtered off
  5. customvolatiles evaporated

Sources & evidence

ORD record
ord-db45ce998b784775a5d668c0c4871b70
Source dataset
uspto-grants-2012_09
Patent number
US08268827B2

Reaction notes

Loading…