[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
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).
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