Sulfuric acid magnesium salt (1:1) → [4-(2-Pyrrolidin-1-yl-ethoxy)-phenyl]-[3-(tetrahydro-pyran-2-yloxy)-benzyl]-amine

HRID 1827521Notes

Reaction equation

HRID 1827521 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:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH:26]=O.S([O-])([O-])(=O)=O.[Mg+2].[BH4-].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.O.CO>[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([NH:15][CH2:26][C:25]3[CH:28]=[CH:29][CH:30]=[C:23]([O:22][CH:17]4[CH2:18][CH2:19][CH2:20][CH2:21][O:16]4)[CH:24]=3)=[CH:13][CH:14]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

9

Reactant 5

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 64937494-(2-(Pyrrolidin-1-yl)ethoxy)anilineHCID 11127426HCID 11127426, compound

Product 1

HCID 22137433[4-(2-Pyrrolidin-1-yl-ethoxy)-phenyl]-[3-(tetrahydro-pyran-2-yloxy)-benzyl]-amineYield 64%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-pyrrolidin-1-yl-ethoxy)-phenylamine (1.92 g, 9.30 mmol) and 3-(tetrahydro-pyran-2-yloxy)-benzaldehyde (2.01 g, 9.76 mmol) in 35 mL methylene chloride was added magnesium sulfate (3.91 g, 32.5 mmol). The reaction mixture was stirred overnight under nitrogen at room temperature. The reaction mixture was filtered and concentrated. The residue was resuspended in 40 mL of 2:1 ethanol:methanol and was treated with sodium borohydride (1.76 g, 46.5 mmol) which was added in portions at room temperature over a period of 1 hr. The reaction was stirred at room temperature overnight. To this mixture was added water and saturated aqueous sodium bicarbonate. The mixture was extracted with methylene chloride and the organic layer was dried (magnesium sulfate), filtered, and concentrated. Medium pressure silica gel chromatography of the residue (methylene chloride to 10% methanol/methylene chloride) afforded 2.34 g (64%) of the title compound. MS 397.2 (M+1)+

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. additionwas added in portions at room temperature over a period of 1 hr
  4. stirringThe reaction was stirred at room temperature overnight
  5. extractionThe mixture was extracted with methylene chloride
  6. dry with materialthe organic layer was dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d1b35467e3f64cbdab8155747ec028e8
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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