2-Methylpiperazine → HCID 91427985, compound

HRID 1830502Notes

Reaction equation

Br[C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.[CH3:21][CH:22]1[CH2:27][NH:26][CH2:25][CH2:24][NH:23]1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>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]>[C:8]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=[CH:10][C:5]([O:4][C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]=2[N:26]2[CH2:25][CH2:24][NH:23][CH:22]([CH3:21])[CH2:27]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-(2-bromo-phenoxy)-biphenyl (0.73 g, 2.25 mmol), rac-2-methylpiperazine (0.285 g, 0.285 mmol), Pd2 dba3 (0.022 g, 1 mol %), rac-binap (0.043 g, 3 mol %) and NaOBut (0.300 g, 3.12 mmol) in dry toluene (15 mL) under argon and stirred at 90° C. overnight. After cooling to room temperature the mixture is filtered and evaporated onto silica gel and and purified by column chromatography eluting with ethyl acetate/heptane 1:2. Yield: 0.264 g (34%). 1H NMR (CDCl3, 500 MHz) 7.55 (m, 2H), 7.49 (m, 2H), 7.38 (m, 2H), 7.27 (m, 1H), 7.10 (m, 1H), 6.90–7.00 (m, 5H), 3.30–3.35 (m, 2H), 2.88 (m, 1H), 2.62–2.80 (m, 3H), 2.30–2.40 (m, 1H) 1.60–2.00 (br, 1H), 0.99 (d, 3H); MS(m/z): 345.1.

Workup

temperatureAfter cooling to room temperature the mixture
filtrationis filtered
customevaporated onto silica gel
custompurified by column chromatography
washeluting with ethyl acetate/heptane 1:2

Sources & evidence

ORD record: ord-c6b05338f16c4f7eb71b9ecb0dde6c07
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067501B2

Reaction notes

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