Triethylamine → 6-Methyl-6-phenyl-1,3-oxazinan-2-one

HRID 2037414Notes

Reaction equation

HRID 2037414 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([OH:6])[CH3:5].Cl[C:14](Cl)([O:16]C(=O)OC(Cl)(Cl)Cl)Cl.CCN(CC)CC>C(Cl)Cl.O>[CH3:5][C:4]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:6][C:14](=[O:16])[NH:1][CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 249751014-Amino-2-phenylbutan-2-ol

Product 1

HCID 534742826-Methyl-6-phenyl-1,3-oxazinan-2-oneYield 59.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-amino-2-phenylbutan-2-ol (5.0 g, 0.03 mol) in CH2Cl2 (50 mL) was added triphosgene (2.97 g, 0.01 mol) and Et3N (9.09 g, 0.09 mol) at 0° C. After stirring for 1 h, the mixture was diluted with water and extracted with CH2Cl2. The organic layer was washed with brine, dried over Na2SO4, concentrated and purified by chromatography to afford 6-methyl-6-phenyl-1,3-oxazinan-2-one (1.14 g, 20%). 1H NMR (CDCl3): 1.60 (s, 3H), 1.80-2.00 (m, 1H), 2.30-2.40 (m, 1H), 3.15-3.21 (m, 1H), 6.00 (s, 1H), 7.30-7.45 (m, 5H), 8.90-9.01 (m, 1H).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by chromatography

Sources & evidence

ORD record
ord-8b69fd35058943c6909a66e332ff31ac
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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