4-Bromophenetole → 2-{-4-[1-(4-Ethoxy-phenyl)-piperidin-4-yl]-phenyl}-N-ethyl-propionamide

HRID 409735Notes

Reaction equation

[CH2:1]([NH:3][C:4](=[O:19])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1)[CH3:6])[CH3:2].Br[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH3:29])=[CH:23][CH:22]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>O1CCOCC1>[CH2:28]([O:27][C:24]1[CH:25]=[CH:26][C:21]([N:16]2[CH2:17][CH2:18][CH:13]([C:10]3[CH:11]=[CH:12][C:7]([CH:5]([CH3:6])[C:4]([NH:3][CH2:1][CH3:2])=[O:19])=[CH:8][CH:9]=3)[CH2:14][CH2:15]2)=[CH:22][CH:23]=1)[CH3:29]

Participants

Conditions

Temperature: 120 °C

Procedure

60 mg (0.23 mmol) N-Ethyl-2-(4-piperidin-4-yl-phenyl)-propionamide (VI.1) are added to a mixture of 46 mg (0.23 mmol) 1-bromo-4-ethoxy-benzene, 91 mg (97%, 0.92 mmol) sodium tert-butyrat, 28 mg (0.09 mmol) 2-(di-tert-butylphosphino)biphenyl and 21 mg (0.02 mmol) tris-(dibenzylidenaceton)-dipalladium(0) in 1.0 mL 1,4-dioxane. The mixture is stirred for 1.5 h at 120° C. in a microwave oven. After that time, the solvent is removed in vacuo and the residue is purified by HPLC (column: Waters XBridge 50; eluent A: water+0.3% NH4OH, eluent B: MeOH) to yield the desired product.

Workup

customAfter that time, the solvent is removed in vacuo
customthe residue is purified by HPLC (column: Waters XBridge 50; eluent A: water+0.3% NH4OH, eluent B: MeOH)

Sources & evidence

ORD record: ord-7a4590e1074647f39303c2a7adec6b9d
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759528B2

Reaction notes

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