Toluene → 2-(Propan-2-yl)-1,3-oxazinane

HRID 276272Notes

Reaction equation

HRID 276272 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[O-]S([O-])(=O)=O.[Mg+2].[C:12]1([CH3:18])[CH:17]=CC=C[CH:13]=1>>[CH:12]([CH:18]1[NH:1][CH2:2][CH2:3][CH2:4][O:5]1)([CH3:17])[CH3:13]

Participants

4

Reactant 3

HCID 1140TolueneHCID 90863-Amino-1-propanolHCID 24083Sulfuric acid magnesium salt (1:1)2×

Product 1

HCID 137649682-(Propan-2-yl)-1,3-oxazinaneYield 61%

Procedure

To a solution of 3-aminopropanol (91 g, 65.4 mmol) in toluene (100 mL) was added isobutraldehyde (9.0 mL, 99.1 mmol, 1.5 equiv.) and MgSO4 (7.5 g) to generate an exotherm. The slurry was stirred for 30 min. and an additional portion of MgSO4 was added (7.5 g), and the slurry was stirred overnight. The resulting mixture was filtered and concentrated under reduced pressure. The condensate was again concentrated under reduced pressure and the two residues were combined to afford 2isopropyltetrahydro-1,3-oxazine as a colorless oil (5.18 g, 61%) 1H NMR (CDCl3) δ0.84-0.88 (m, 6H), 1.24-1.29 (m, 1H), 1.51-1.66 (m, 3H), 2.77-2.87 (m, 1H), 3.07-3.13 (m, 1H), 3.60-3.76 (m, 2H), 4.00-4.05 (m, 1H).

Workup

  1. stirringthe slurry was stirred overnight
  2. filtrationThe resulting mixture was filtered
  3. concentrationconcentrated under reduced pressure
  4. concentrationThe condensate was again concentrated under reduced pressure

Sources & evidence

ORD record
ord-3ddc3499d80f4260b380a459a5a96ee3
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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