P-Anisidine → HCID 21939765, compound

HRID 1242874Notes

Reaction equation

HRID 1242874 reaction equation
[N:1]1([CH2:7][CH2:8][CH:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH2:20][C:21]4[CH:29]=[CH:28][C:24]([C:25]([O-])=[O:26])=[CH:23][CH:22]=4)[CH:15]=3)[CH2:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:30][O:31][C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1.C1C=CC2N(O)N=NC=2C=1.C(=O)([O-])[O-].[K+].[K+]>CN(C1C=CN=CC=1)C.C(OCC)(=O)C.C1COCC1.O.CN(C=O)C>[CH3:30][O:31][C:32]1[CH:38]=[CH:37][C:35]([NH:36][C:25](=[O:26])[C:24]2[CH:28]=[CH:29][C:21]([CH2:20][O:19][C:14]3[CH:13]=[C:12]4[C:17](=[CH:16][CH:15]=3)[CH2:18][CH:9]([CH2:8][CH2:7][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[CH2:10][CH2:11]4)=[CH:22][CH:23]=2)=[CH:34][CH:33]=1

Participants

10

Reactant 4

HCID 7732P-AnisidineHCID 11430Potassium CarbonateHCID 757711-HydroxybenzotriazoleHCID 21939875HCID 21939875, compound

Product 1

HCID 21939765HCID 21939765, compoundYield 65.2%

Reagents, catalysts & solvents 5

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

WSCD (0.11 ml) was added to DMF solution (2 ml) of 4-[[2-(2-piperidinoethyl)-6-tetralinyl]oxymethyl]benzoate (170 mg), 4-methoxyaniline (53 mg), HOBt (70 mg) and DMAP (60 mg) at room temperature, which was stirred for 12 hours. 10% aqueous potassium carbonate solution and water was added to the reaction mixture, and extraction was conducted using a mixed solution of THF and ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride solution, dried, and then concentrated. The residue was purified using alumina column chromatography (development solvent: THF), and recrystallized (THF-IPE) to give the titled compound (140 mg).

Workup

  1. washThe organic layer was washed with water and saturated aqueous sodium chloride solution
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified
  5. customrecrystallized (THF-IPE)

Sources & evidence

ORD record
ord-ae71f5415332490ba0724407af1ff4fc
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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