Chloroform → 4-Phenylmorpholine

HRID 1014786Notes

Reaction equation

HRID 1014786 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.CC([O-])(C)C.[Na+].C(Cl)(Cl)Cl>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].C1(P(C2C=CC=CC=2)C2[C-](N(C)C)C=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2]>[C:2]1([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6212ChloroformHCID 7961BromobenzeneHCID 8083MorpholineHCID 23676156Sodium t-butoxide

Product 1

HCID 623394-PhenylmorpholineYield 82.1%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1317290462-Diphenylphosphino-dimethylaminoferroceneCatalystHCID 1140TolueneSolvent

Procedure

According to General Procedure B, a mixture of bromobenzene (53 μL, 0.50 mmol), morpholine (52 μL, 0.60 mmol), NaOt-Bu (67 mg, 0.70 mmol), Pd2(dba)3.CHCl3 (10 mg, 0.01 mmol) and 12f (8 mg, 0.02 mmol) in PhMe (2.5 mL), was heated, cooled and filtered. Column chromatography (6:1:93 Et2O/Et3N/hexane, silica gel) gave 52h (67 mg, 82%) as a colorless solid. 1H NMR (600 MHz, CDCl3) δ 7.32 (t, 2H, J=4.2 Hz), 6.97-6.91 (m, 3H), 3.90 (t, 4H, J=2.4 Hz), 3.19 (t, 4H, J=2.4 Hz); 13C NMR (150.9 MHz, CDCl3) δ 151.3, 129.2, 120.1, 115.7, 67.0, 49.4.

Workup

  1. temperaturecooled
  2. filtrationfiltered

Sources & evidence

ORD record
ord-d3a6ee6656d841baa9c3cc2e00550eec
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

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