4-Bromophenetole → 2-{4-[1-(4-Ethoxy-phenyl)-piperidin-4-yl]-phenyl}-propionic acid

HRID 409732Notes

Reaction equation

C[O:2][C:3](=[O:18])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1)[CH3:5].Br[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH3:28])=[CH:22][CH:21]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>O1CCOCC1>[CH2:27]([O:26][C:23]1[CH:24]=[CH:25][C:20]([N:15]2[CH2:16][CH2:17][CH:12]([C:9]3[CH:10]=[CH:11][C:6]([CH:4]([CH3:5])[C:3]([OH:2])=[O:18])=[CH:7][CH:8]=3)[CH2:13][CH2:14]2)=[CH:21][CH:22]=1)[CH3:28]

Participants

Conditions

Temperature: 70 °C

Procedure

1.00 g (4.04 mmol) 2-(4-Piperidin-4-yl-phenyl)-propionic acid methyl ester (XI.3) are added to a mixture of 813 mg (4.04 mmol) 1-bromo-4-ethoxy-benzene, 1.60 g (97%, 16.2 mmol) sodium tert-butyrat, 483 mg (1.62 mmol) 2-(di-tert-butylphosphino)biphenyl and 370 mg (0.40 mmol) tris-(dibenzylidenaceton)-dipalladium(0) in 10 mL 1,4-dioxane. The mixture is stirred for 12 h at 70° C. After that time, the precipitate is filtered off and washed with ACN and diethyl ether. 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

filtrationAfter that time, the precipitate is filtered off
washwashed with ACN and diethyl ether
customThe residue is purified by HPLC (column: Waters XBridge 50; eluent A: water+0.3% NH4OH, eluent B: MeOH)

Sources & evidence

ORD record: ord-231ffbaf321c48d4b9ccb408ca3d3bcf
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759528B2

Reaction notes

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