4-Piperidinecarboxylic acid, 1-methyl-, methyl ester

To a stirred solution of methyl isonipecotate (L. OOG, 7.00 mmol) in methanol (25 ml) was added formic acid (5.52g, 12.00 mmol) and a solution of formaldehyde (2.67g, 35.00 mmol, 40percent aqueous) and the reaction heated at reflux. After 3 hours the reaction was cooled and concentrated under reduced pressure. The aqueous solution was basified with NAHC03 and extracted with DCM (3 x 30 ml), dried (MGSO4) and concentrated under reduced pressure to give a brown liquid (L. OOG, 910-.) ; b (270 MHz; CDC13 ; Me4Si), 1.69-2. 03 (6 H, m), 2.23-2. 32 (4H, m), 2.78- 2.83 (2H, m), 3.68 (3 H, s); M/Z (APCI) 158 (100percent [M+H] +), 126 (33, C7H120N).To a stirred solution of 1-methylisonipecotic acid hydrochloride (178.64 g, 1 mol) in 350 mL of methanol (8 equivalents) was added, dropwise with stirring and cooling (ice-salt bath) to -10° C., 112.8 mL (1.55 equivalents) of thionyl chloride. To a stirred solution of methyl isonipecotate (L. OOG, 7.00 mmol) in methanol (25 ml) was added formic acid (5.52g, 12.00 mmol) and a solution of formaldehyde (2.67g, 35.00 mmol, 40percent aqueous) and the reaction heated at reflux. After 3 hours the reaction was cooled and concentrated under reduced pressure. The aqueous solution was basified with NAHC03 and extracted with DCM (3 x 30 ml), dried (MGSO4) and concentrated under reduced pressure to give a brown liquid (L. OOG, 910-.) ; b (270 MHz; CDC13 ; Me4Si), 1.69-2. 03 (6 H, m), 2.23-2. 32 (4H, m), 2.78- 2.83 (2H, m), 3.68 (3 H, s); M/Z (APCI) 158 (100percent [M+H] +), 126 (33, C7H120N).To a stirred solution of 1-methylisonipecotic acid hydrochloride (178.64 g, 1 mol) in 350 mL of methanol (8 equivalents) was added, dropwise with stirring and cooling (ice-salt bath) to -10° C., 112.8 mL (1.55 equivalents) of thionyl chloride.

Molecular Weight:157.21
XLogP3:0.6
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:157.110278721
Monoisotopic Mass:157.110278721
Topological Polar Surface Area:29.5
Heavy Atom Count:11
Complexity:139
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes