[CH3:1][C:2](=O)[CH2:3][CH2:4][C:5](=O)[CH3:6].[NH2:9][CH2:10][CH2:11][CH2:12][OH:13]>[Pd].C(O)C>[OH:13][CH2:12][CH2:11][CH2:10][N:9]1[CH:2]([CH3:1])[CH2:3][CH2:4][CH:5]1[CH3:6]A total of 3 moles of 2,5-hexanedione, 3 moles of 3-amino-1propanol, 10 g of 10% Pd/C, and 500 ml of ethanol were charged to an autoclave. The reaction mixture was pressured up to 1100 psi of H2 and kept for 3 hours at 100° C. Distillation yielded 170 g of N-(3-hydroxypropyl)-2,5-dimethylpyrrolidine (b.p.=119° C. at 25 mm).
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