Propanal → HCID 14151579, compound

HRID 2414181Notes

Reaction equation

HRID 2414181 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% Pd/C catalyst is hydrogenated at 40 psi (3 atmosphere 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, melting point 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-3e31d92bbc524504a5538e3894c16f7e
Source dataset
uspto-grants-1988_01
Patent number
US04721787

Reaction notes

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