Propanal → HCID 14151579, compound

HRID 364133Notes

Reaction equation

HRID 364133 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]2[O:17][CH2:16][CH:11]3[NH:12][CH2:13][CH2:14][CH:15]=[C:10]3[C:8]=2[CH:9]=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+].[CH:27](=O)[CH2:28][CH3:29]>O.[Pd]>[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]2[O:17][CH2:16][C@H:11]3[N:12]([CH2:27][CH2:28][CH3:29])[CH2:13][CH2:14][CH2:15][C@@H:10]3[C:8]=2[CH:9]=1

Participants

7

Reactant 4

HCID 527PropanalHCID 702EthanolHCID 10340Sodium CarbonateHCID 14151577HCID 14151577, compound

Product 1

HCID 14151579HCID 14151579, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 14 g of 9-methoxy-2,3,4a,5-tetrahydro-4H-[1]-benzopyrano[3,4-b]pyridine hydrochloride, 140 ml of ethanol, and a solution of 2.95 g of sodium carbonate in 10 ml of water and 3 g of 10% palladium on carbon catalyst is hydrogenated at 3 atm. pressure and 50° for 16 hours. After the addition of 15 g of propionaldehyde the hydrogenation is continued for an additional 16 hours under the same conditions. After filtration, the solvent is removed in vacuo. The residue is dissolved in ethanol and acidified with ethanolic hydrogen chloride to afford trans-9-methoxy-4-propyl-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine hydrochloride, m.p. 252°-254° (the compound of Example 2a).

Workup

  1. filtrationAfter filtration
  2. customthe solvent is removed in vacuo
  3. dissolutionThe residue is dissolved in ethanol

Sources & evidence

ORD record
ord-68f1d2d7ae4f430eb2e4f7f620005b6f
Source dataset
uspto-grants-1986_08
Patent number
US04604397

Reaction notes

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