Sulfuric acid magnesium salt (1:1) → [4-(2-Pyrrolidin-1-yl-ethoxy)-phenyl]-[4-(tetrahydro-pyran-2-yloxy)-benzylidene]-amine

HRID 1827561Notes

Reaction equation

HRID 1827561 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[O:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]1[O:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([N:15]=[CH:27][C:26]3[CH:25]=[CH:24][C:23]([O:22][CH:17]4[CH2:18][CH2:19][CH2:20][CH2:21][O:16]4)=[CH:30][CH:29]=3)=[CH:13][CH:14]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 64937494-(2-(Pyrrolidin-1-yl)ethoxy)anilineHCID 112527364-(2-Tetrahydro-2H-pyranoxy)benzaldehyde

Product 1

HCID 22137358[4-(2-Pyrrolidin-1-yl-ethoxy)-phenyl]-[4-(tetrahydro-pyran-2-yloxy)-benzylidene]-amineYield 100.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-pyrrolidin-1-yl-ethoxy)-phenylamine (6.92 g, 33.5 mmol) and 4-(tetrahydro-pyran-2-yloxy)-benzaldehyde (7.25 g, 35.2 mmol) in 110 mL methylene chloride was added magnesium sulfate (14.2 g, 117.3 mmol). The reaction mixture was stirred at room temperature overnight under nitrogen. The reaction was filtered and concentrated to afford 13.3 g of the crude title compound of Step A which was used without further purification. MS 395.2 (M+1)+

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4e8070cd2fab4b04af5c745f8716d90e
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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