2-Morpholinoethylamine → HCID 66893941, compound

HRID 1162000Notes

Reaction equation

HRID 1162000 reaction equation
I[C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[NH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.CC([O-])(C)C.[Na+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1(C)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]>[N:17]1([CH2:16][CH2:15][NH:14][C:2]2[C:10]3[O:9][CH:8]=[CH:7][C:6]=3[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=2)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 4082852-MorpholinoethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 21864764HCID 21864764, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 66893941HCID 66893941, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 7237O-XyleneSolvent

Procedure

7-Iodo-5-nitrobenzofuran (1.00 g, 3.46 mmol), 4-(2-aminoethyl)morpholine (0.54 g, 4.15 mmol), NaOt-Bu (0.47 g, 0.00484 mol), Xantphos (0.20 g, 0.346 mmol) and Pd2 dba3 (80 mg, 0.0865 mol) were heated in xylene (20 mL) at 120° C. for 1.5 hours. The reaction mixture was filtered through Celite and the solvent evaporated. The residue was run through a silica plug using dichloromethane (DCM) and then a 90:9:1 mixture of DCM/MeOH/NH3 (aqueous 25%) as eluents. The product-containing fractions were concentrated to yield 0.978 g (97%) of the title compound as a dark yellow oil. HPLC purity=97%, m/z=292 (M+H)+, 1H NMR (270 MHz, CDCl3) δ ppm 2.44-2.61 (m, 4H) 2.75 (t, J=5.81 Hz, 2H) 3.31-3.43 (m, 2H) 3.69-3.82 (m, 4H) 6.85 (d, J=1.98 Hz, 1H) 7.36 (d, J=1.98 Hz, 1H) 7.70 (d, J=1.98 Hz, 1H) 7.90 (d, J=2.23 Hz, 1H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent evaporated
  3. additiona 90:9:1 mixture of DCM/MeOH/NH3 (aqueous 25%) as eluents
  4. concentrationThe product-containing fractions were concentrated

Sources & evidence

ORD record
ord-af2c70dbc8dd4fa0bca5611b8d87fa2f
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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