Acetic Acid → HCID 18914135, compound

HRID 1292068Notes

Reaction equation

HRID 1292068 reaction equation
[CH3:1][C:2]1[C:14]2[N:13]3[C:8]([CH:9]=[CH:10][CH:11]=[CH:12]3)=[CH:7][C:6]=2[C:5]([NH:15][CH2:16][CH2:17][CH2:18][N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[N:4][N:3]=1.C(O)(=O)C.CO>C(Cl)Cl.[Pd]>[CH2:22]([N:19]([CH2:20][CH3:21])[CH2:18][CH2:17][CH2:16][NH:15][C:5]1[C:6]2[CH:7]=[C:8]3[N:13]([C:14]=2[C:2]([CH3:1])=[N:3][N:4]=1)[CH2:12][CH2:11][CH2:10][CH2:9]3)[CH3:23]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 887Methanol2×HCID 9818210HCID 9818210, compound

Product 1

HCID 18914135HCID 18914135, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

4-(Methyl)-N,N-diethyl-N'-[pyridazino[4,5-b]indolizin-1-yl]-1,3-propanediamine (2.75 g, 8.83 mmoL) was hydrogenated in a Parr appartus with 10% Pd on charcoal (0.54 g) in a 1:1 mixture of acetic acid and methanol at 55 psi and room temperature. Filtration through Solka Floc to remove the catalyst and evaporation of the filtrate gave a crude product which was passed through a pad of alumina eluting with 5% methanol in methylene chloride to give the free base of the title product in quantitative yield. The free base was converted to the monofumarate salt: m.p.171°-172° C.

Workup

  1. filtrationFiltration through Solka Floc
  2. customto remove
  3. customthe catalyst and evaporation of the filtrate
  4. customgave a crude product which

Sources & evidence

ORD record
ord-bdb3a80410d8445dac3eed64e6bb5e3d
Source dataset
uspto-grants-1998_05
Patent number
US05756501

Reaction notes

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