Ammonia → 4-[1-(2-Benzyloxyethyl)piperidin-4-yl]butyramide

HRID 2250317Notes

Reaction equation

C[O:2][C:3](=O)[CH2:4][CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9][CH2:8]1.[NH3:24]>CO>[CH2:16]([O:15][CH2:14][CH2:13][N:10]1[CH2:11][CH2:12][CH:7]([CH2:6][CH2:5][CH2:4][C:3]([NH2:24])=[O:2])[CH2:8][CH2:9]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Compound 3a (1.30 g, 4.0 mmol) was dissolved in 7 N NH3 in methanol (25 mL) in a sealed tube. The resulting solution was stirred at 50° C. for 3 days. After that the solvent was removed under vacuum and the residue was purified by Flash™ chromatography (BIOTAGE, Inc) (9.5:0.45:0.05 dichloromethane/methanol/concentrated ammonium hydroxide, v/v) to provide 4a (0.93 g, 78%) as a white solid. 1H NMR (300 MHz, CD3OD) δ 1.27 (m, 5H), 1.65 (m, 4H), 2.11 (m, 4H), 2.65 (m, 2H), 2.96 (d, 2H), 3.62 (m, 2H), 4.51 (s, 2H), 7.37 (m, 5H). m/z (ESI): 305 [C18H28N2O2+H]+.

Workup

customAfter that the solvent was removed under vacuum
customthe residue was purified by Flash™ chromatography (BIOTAGE, Inc) (9.5:0.45:0.05 dichloromethane/methanol/concentrated ammonium hydroxide, v/v)

Sources & evidence

ORD record: ord-92b11819b43245b2b283efbaf7403003
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07317013B2

Reaction notes

Loading…