Hydrochloric Acid → HCID 67618169, compound

HRID 1029727Notes

Reaction equation

HRID 1029727 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][CH2:10][NH:11][N:12]1[C:20]2[C:15](=[CH:16][C:17]([O:21]CC3C=CC=CC=3)=[CH:18][CH:19]=2)[CH:14]=[CH:13]1.[H][H].[ClH:31]>C(O)C.CO.CCOCC.[Pd]>[ClH:31].[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][CH2:10][NH:11][N:12]1[C:20]2[C:15](=[CH:16][C:17]([OH:21])=[CH:18][CH:19]=2)[CH:14]=[CH:13]1

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 67619530HCID 67619530, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67618169HCID 67618169, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

In a 500 ml Parr hydrogenation bottle, 10% Pd/C (1.5 g) was suspended in 50 ml ethanol, and to this was added a solution of 1-[(3-fluoro-4-pyridinyl)propylamino]-5-phenylmethoxy-1H-indole (15.0 g) in 200 ml ethanol. The mixture was shaken under 50 psi hydrogen gas for three hours at 50° C. Upon cooling, the mixture was filtered, and the filtrate was concentrated to give a solid, 11.4 g. This material was eluted on a silica gel column with ethyl acetate/dichloromethane (1:3) via HPLC, and the desired fractions were concentrated to give a solid, 8.5 g, m.p. 90°-95° C. A 2.0 g sample of this material was dissolved in 50 ml methanol, the pH was adjusted to 1 with ethereal HCl, and the solution was diluted with 200 ml ether. The resultant precipitate was collected and dried to give 2.1 g of the product, m.p. 218° C. (dec.).

Workup

  1. temperatureUpon cooling
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customto give a solid, 11.4 g
  5. washThis material was eluted on a silica gel column with ethyl acetate/dichloromethane (1:3) via HPLC
  6. concentrationthe desired fractions were concentrated
  7. customto give a solid, 8.5 g, m.p. 90°-95° C
  8. customThe resultant precipitate was collected
  9. customdried

Sources & evidence

ORD record
ord-f3414b8f30e5488d9a1bb81a12444a94
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

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