Water → HCID 12988890, compound

HRID 2184943Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=2)[C:18]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[O:19])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([C:15]2[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=2)[C:18]([N:20]([CH2:21][CH3:22])[CH2:23][CH3:24])=[O:19])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 3-[N-(1-benzyl-piperidin-4-yl)-amino]-N,N-diethyl benzamide (compound 10) (360 mg, 0.98 mmol), Ph3Bi (1.10 g, 2.50 mmol), and Cu(OAc)2 (0.45 g, 2.48 mmol) in toluene (10 mL) was heated at 110° C. for 12 h. Another portion of Cu(OAc)2 (0.45 g) was added and the mixture was heated at 110° C. for an additional 12 h and allowed to cool to room temperature. Water (10 mL) was added and the mixture filtered through Celite®. The layers in the filtrate were separated, and the organic phase was washed with water, brine, dried over Na2SO4 and concentrated. Chromatography of the residue (9:1 EtOAc/heptane) gave the tide compound 11 (255 mg, 59%) as a pale yellow thick oil.

Workup

temperaturethe mixture was heated at 110° C. for an additional 12 h
temperatureto cool to room temperature
filtrationthe mixture filtered through Celite®
customThe layers in the filtrate were separated
washthe organic phase was washed with water, brine
dry with materialdried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-5905a0a89fe5425d9b90cd9780df6bc0
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06399635B1

Reaction notes

Loading…