Dichloromethane → HCID 57085494, compound

Trifluoroacetic acid (10 ml) was added to a solution of N-[(1-tert-butoxycarbonyl-4-piperidyl)methyl]pyridine-3-carboxamide (1.56 g) in dichloromethane (25 ml) and the mixture stirred for 2 hours then the solvent was removed in vacuo. The residue was dissolved in dry acetonitrile (10 ml) and potassium carbonate (5.0 g) was added, followed by a solution of (R)-7-chloro-1,4-benzodioxan-2-ylmethyl 4-toluenesulphonate (1.7 g) in dry acetonitrile (15 ml), and the mixture was stirred and heated under reflux for 6 hours. The cooled mixture was poured into water then extracted with dichloromethane (2×100 ml). The combined extracts were washed with brine (100 ml), dried over magnesium sulphate, and the solvent removed in vacuo. The residue was purified by flash chromatography over silica eluting with a 20:1 mixture of dichloromethane and methanol. Appropriate fractions were combined and the solvent removed in vacuo to give (S)-N-{[1-(8-chloro-1,4-benzodioxan-2-ylmethyl)-4-piperidyl]methyl}pyridine-3-carboxamide (1.04 g) as a colourless solid m.p. 52-54° C. [α]D -35.3° (c=1.024, methanol).

1. customthe solvent was removed in vacuo
2. dissolutionThe residue was dissolved in dry acetonitrile (10 ml)
3. additionpotassium carbonate (5.0 g) was added
4. stirringthe mixture was stirred
5. temperatureheated
6. temperatureunder reflux for 6 hours
7. additionThe cooled mixture was poured into water
8. extractionthen extracted with dichloromethane (2×100 ml)
9. washThe combined extracts were washed with brine (100 ml)
10. dry with materialdried over magnesium sulphate
11. customthe solvent removed in vacuo
12. customThe residue was purified by flash chromatography over silica eluting with a 20:1 mixture of dichloromethane and methanol
13. customthe solvent removed in vacuo

ORD record

ord-c13717a3418a4a2995b000475a84f712

Source dataset

uspto-grants-1999_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05935973