1-(4-Methoxyphenyl)piperazine → HCID 54591512, compound

HRID 509251Notes

Reaction equation

[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12](=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15](Br)[N:14]=1)[CH2:8]2.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:25][CH:24]=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>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12](=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N:32]3[CH2:31][CH2:30][N:29]([C:26]4[CH:25]=[CH:24][C:23]([O:22][CH3:21])=[CH:28][CH:27]=4)[CH2:34][CH2:33]3)[N:14]=1)[CH2:8]2

Participants

Conditions

Temperature: 100 °C

Procedure

N-(adamantan-2-yl)-6-bromopicolinamide (55 mg, 0.194 mmol), 1-(4-methoxyphenyl)piperazine (41 mg, 0.213 mmol), Pd2(dba)3 (3.5 mg, 0.00388 mmol), xantphos (6.7 mg, 0.0116 mmol), and sodium-tert-butoxide (27.4 mg, 0.285 mmol) were suspended in toluene (3 ml), and then stirred at 100° C. under nitrogen stream for 3 hours. The resulting reaction liquid was concentrated under reduced pressure, and then the residue thus obtained was subjected to MPLC (30% EtOAc/Hexanes), to obtain 64 mg of pale yellow solid (84%). MS (ESI): 447 [M+H]+

Workup

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

Sources & evidence

ORD record: ord-18fca24cde684475a8e24e339eae0bc3
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096571B2

Reaction notes

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