Triethylamine → HCID 53414002, compound

Temperature

50 °C

1-Benzyl-3-piperidone hydrochloride (700 mg, 2.7 mmol), triethylamine (270 mg, 2.7 mmol) and 1-(tert-butoxycarbonyl)-piperizine (500 mg, 2.7 mmol) in DCM, was stirred at rt for 1 h, then heated to 50° C. for 40 min. Sodium triacetoxyborahydride (1.12 g, 5.3 mmol) was added and the reaction mixture allowed to cool, with stirring, over 12 h then concentrated to dryness in vacuo. The residue was partioned between DCM/water, the organics dried (MgSO4) and concentrated to dryness in vacuo. The resulting residue in EtOH (10 ml) was hydrogenated with 10% w/w palladium on carbon (200 mg) under hydrogen at rt for 18 h. The reaction was filtered through celite and concentrated to dryness in vacuo to give 3-piperazine-1-yl-piperidine as a pale yellow gum (700 mg, 2.6 mmol, 97%). 8H (CDCl3, 300K) 3.43-3.37 (4H, m br), 3.21 (1H, d br, J=11.6 Hz), 3.01 (1H, d br, J=12.2 Hz), 2.59-2.47 (6H, m br), 2.45-2.38 (1H, m), 1.99-1.92 (1H, m br), 1.82-1.75 (1H, m), 1.58-1.48 (1H, m), 1.45 (9H, s), 1.42-1.33 (1H, m). m/z (ES+, 70V) 270.3 (MH+).

1. temperatureto cool
2. concentrationthen concentrated to dryness in vacuo
3. dry with materialthe organics dried (MgSO4)
4. concentrationconcentrated to dryness in vacuo
5. waitThe resulting residue in EtOH (10 ml) was hydrogenated with 10% w/w palladium on carbon (200 mg) under hydrogen at rt for 18 h
6. filtrationThe reaction was filtered through celite and
7. concentrationconcentrated to dryness in vacuo

ORD record

ord-29c475f554ff498189355c183c047c0a

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156811B2