Chloroform → 4-(2-Nitrophenyl)morpholine

HRID 1014784Notes

Reaction equation

HRID 1014784 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1Cl)([O-:3])=[O:2].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]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]>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 6212ChloroformHCID 69451-Chloro-2-nitrobenzeneHCID 8083MorpholineHCID 23676156Sodium t-butoxide

Product 1

HCID 963654-(2-Nitrophenyl)morpholineYield 43.2%

Reagents, catalysts & solvents 3

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

Procedure

According to General Procedure B, a mixture of 2-nitro chlorobenzene (79 mg, 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 (0.4 mL of 0.05 M solution in PhMe) in PhMe (2.5 mL) was heated, cooled and filtered. Evaporation of the solvent under reduced pressure and column chromatography of the pre-adsorbed crude material (40% Et2O in hexane, silica gel) gave 52d (45 mg, 43%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.79 (d, 1H, J=8.1 Hz), 7.52-7.47 (m, 1H), 7.15 (d, 1H, J=8.3 Hz), 7.10-7.06 (m, 1H), 3.85-3.83 (m, 4H), 3.07-3.04 (m, 4H); 13C NMR (75.5 MHz, CDCl3) δ 145.8, 143.7, 133.5, 125.9, 122.3, 120.9, 66.8, 52.1.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. customEvaporation of the solvent under reduced pressure and column chromatography of the pre-adsorbed crude material (40% Et2O in hexane, silica gel)

Sources & evidence

ORD record
ord-4094141bf9ac4df780578646757dbecf
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

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