3-Methoxypropylamine → HCID 66786128, compound

HRID 1096666Notes

Reaction equation

HRID 1096666 reaction equation
[CH3:1][C:2]([CH:5]=O)([CH3:4])[CH3:3].[CH3:7][O:8][CH2:9][CH2:10][CH2:11][NH2:12].S([O-])([O-])(=O)=O.[Mg+2].CC1C=CC(S([CH2:29][N+:30]#[C-:31])(=O)=O)=CC=1>ClCCl>[C:2]([C:5]1[N:12]([CH2:11][CH2:10][CH2:9][O:8][CH3:7])[CH:31]=[N:30][CH:29]=1)([CH3:1])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 16723-Methoxypropylamine2×HCID 12417PivalaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 161915Tosylmethyl isocyanide

Product 1

HCID 66786128HCID 66786128, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 50 mL round bottomed flask was added pivaldehyde (500 mg, 5.8 mmol), 3-methoxypropylamine (569 mg, 6.4 mmol) and magnesium sulfate. Dichloromethane (20 mL) was added and the mixture was stirred overnight under nitrogen. The mixture was filtered through a pad of Celite and the solvent was removed form the filtrate under vacuum. The residue was dissolved in methanol (10 mL); 3-methoxypropylamine (466 mg, 5.2 mmol) and TOSMIC (942 mg, 4.8 mmol) was added and the mixture was again stirred overnight. Solvent was removed under vacuum, and the residue was purified by preparatory LC/MS (10-25% CH3CN in H2O) to give 5-tert-butyl-1-(3-methoxypropyl)-1H-imidazole (133A) as a yellow oil (376 mg, 40% yield). ESI-MS:m/z 197.4 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. customthe solvent was removed form the filtrate under vacuum
  3. dissolutionThe residue was dissolved in methanol (10 mL)
  4. waitthe mixture was again stirred overnight
  5. customSolvent was removed under vacuum
  6. customthe residue was purified by preparatory LC/MS (10-25% CH3CN in H2O)

Sources & evidence

ORD record
ord-da9dce6627a743a69b832d06ac47764d
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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