1-(4-Methoxyphenyl)piperazine → HCID 54591433, compound

HRID 509249Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][CH2:13][C:12]([CH3:17])([CH3:16])[CH2:11]2)=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[CH3:16][C:12]1([CH3:17])[CH2:13][CH2:14][CH2:15][N:10]([C:8]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([N:29]3[CH2:28][CH2:27][N:26]([C:23]4[CH:22]=[CH:21][C:20]([O:19][CH3:18])=[CH:25][CH:24]=4)[CH2:31][CH2:30]3)[N:7]=2)=[O:9])[CH2:11]1

Participants

Conditions

Temperature: 100 °C

Procedure

(6-bromopyridin-2-yl)(3,3-dimethylpiperidin-1-yl)methanone (40 mg, 0.135 mmol), 1-(4-methoxyphenyl)piperazine (29 mg, 0.149 mmol), Pd2(dba)3 (2.5 mg, 0.00273 mmol), xantphos (4.7 mg, 0.00812 mmol), and sodium-tert-butoxide (19.0 mg, 0.198 mmol) were suspended in toluene (2 ml), and then stirred at 100° C. under nitrogen stream for 2 hours. The resulting reaction liquid was concentrated under reduced pressure, and then the residue thus obtained was subjected to MPLC (50% EtOAc/Hexanes), to obtain 47 mg of pale yellow solid (85%). MS (ESI): 409 [M+H]+

Workup

customThe resulting reaction liquid
concentrationwas concentrated under reduced pressure
customthe residue thus obtained

Sources & evidence

ORD record: ord-16f93a6a555c41dd84d03720984ddab6
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096571B2

Reaction notes

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