2,6-Dichloroaniline → [4-(4-Benzyl-morpholin-2-yl)-phenyl]-(2,6-dichloro-phenyl)-amine

HRID 571776Notes

Reaction equation

C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[CH2:47]([N:54]1[CH2:59][CH2:58][O:57][CH:56]([C:60]2[CH:65]=[CH:64][C:63](Br)=[CH:62][CH:61]=2)[CH2:55]1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.[Cl:67][C:68]1[CH:74]=[CH:73][CH:72]=[C:71]([Cl:75])[C:69]=1[NH2:70].CC([O-])(C)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]>[CH2:47]([N:54]1[CH2:59][CH2:58][O:57][CH:56]([C:60]2[CH:65]=[CH:64][C:63]([NH:70][C:69]3[C:68]([Cl:67])=[CH:74][CH:73]=[CH:72][C:71]=3[Cl:75])=[CH:62][CH:61]=2)[CH2:55]1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of BINAP (112.45 mg; 0.18 mmol) in degassed toluene (20 mL) was added 4-benzyl-2-(4-bromo-phenyl)-morpholine (1.00 g; 3.01 mmol), 2,6-dichloroaniline (0.49 g; 3.01 mmol), Pd2(dba)3 (55.12 mg; 0.06 mmol) and NaOtBu (0.29 g; 3.01 mmol). The resulting mixture was heated at 100° C. for 18 h. After cooling to RT the resulting mixture was filtered over kieselguhr, rinsed with CH2Cl2, and concentrated in vacuo. The residue was purified by column chromatography (Et2O:hexanes 1:3) to afford [4-(4-benzyl-morpholin-2-yl)-phenyl]-(2,6-dichloro-phenyl)-amine (0.73 g).

Workup

temperatureAfter cooling to RT the resulting mixture
filtrationwas filtered over kieselguhr
washrinsed with CH2Cl2
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (Et2O:hexanes 1:3)

Sources & evidence

ORD record: ord-5319c3ecfdbd49ef8842eff46fc644a6
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029371B2

Reaction notes

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