N-((1S)-1-(4-Bromophenyl)ethyl)acetamide → HCID 71617627, compound

HRID 1617323Notes

Reaction equation

[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1)[CH2:2][CH3:3].Br[C:18]1[CH:23]=[CH:22][C:21]([C@@H:24]([NH:26][C:27](=[O:29])[CH3:28])[CH3:25])=[CH:20][CH:19]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>O1CCOCC1>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:12][CH2:13][N:14]([C:18]3[CH:23]=[CH:22][C:21]([C@@H:24]([NH:26][C:27](=[O:29])[CH3:28])[CH3:25])=[CH:20][CH:19]=3)[CH2:15][CH2:16]2)=[CH:7][CH:6]=1)[CH2:2][CH3:3]

Participants

Conditions

Temperature: 70 °C

Procedure

80 mg (0.37 mmol) 4-(4-Propoxy-phenyl)-piperidine (II.3) are added to a mixture of 88 mg (0.37 mmol) (S)—N-[1-(4-bromo-phenyl)-ethyl]-acetamide (III.1), 145 mg (97%, 1.46 mmol) sodium tert-butyrat, 44 mg (0.15 mmol) 2-(di-tert-butylphosphino)biphenyl and 33 mg (0.036 mmol) tris-(dibenzylidenaceton)-dipalladium(0) in 2.0 mL 1,4-dioxane. The mixture is stirred for 12 h at 70° C. After that time, the mixture is filtered over celite, the solvent is removed in vacuo and the residue is purified by HPLC (column: Waters XBridge 5 μM; eluent A: water+0.3% NH4OH, eluent B: MeOH) to yield the desired product.

Workup

filtrationAfter that time, the mixture is filtered over celite
customthe solvent is removed in vacuo
customthe residue is purified by HPLC (column: Waters XBridge 5 μM; eluent A: water+0.3% NH4OH, eluent B: MeOH)

Sources & evidence

ORD record: ord-c2e02e5eb6b84f778005a9e18d6176d7
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765959B2

Reaction notes

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