Benzophenone imine → HCID 86670013, compound

HRID 920554Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH:12]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21](=[NH:34])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC([O-])(C)C.[Na+].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[C:21](=[N:34][C:17]1[CH:18]=[CH:19][C:14]([CH:12]2[O:11][CH2:10][CH2:9][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:13]2)=[CH:15][CH:16]=1)([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a degassed solution of 4-benzyl-6-(4-bromo-phenyl)-morpholine (4.00 g; 12.04 mmol) in toluene (50 mL) was added benzophenone imine (2.42 mL; 14.45 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.60 g; 0.96 mmol), tris-(dibenzylideneacetone)-dipalladium(0) (0.22 g; 0.24 mmol) and NaOtBu (1.62 g; 16.86 mmol). The resulting mixture was heated to 100° C. for 16 hours. After cooling to RT a 5% aqueous NaHCO3 solution was added, and the product was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O:hexanes 1:1) to afford benzhydrylidene-[4-(4-benzyl-morpholin-2-yl)-phenyl]-amine (3.30 g).

Workup

additionwas added
extractionthe product was extracted with EtOAc
dry with materialThe combined organic layers were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (SiO2, Et2O:hexanes 1:1)

Sources & evidence

ORD record: ord-07e21d9cbd0849e5a2446532b66c8c3f
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273017B2

Reaction notes

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