Triethylamine → 1-(1-Boc-4-piperidyl)-4-methyl-3,1-benzoxazin-2-one

HRID 1377702Notes

Reaction equation

HRID 1377702 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)[OH:3].Cl[C:25](Cl)([O:27]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C>C1COCC1>[C:17]([N:14]1[CH2:13][CH2:12][CH:11]([N:10]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[CH:2]([CH3:1])[O:3][C:25]2=[O:27])[CH2:16][CH2:15]1)([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 57248020methyl-(2-(1-Boc-4-piperidinylamino)phenyl) carbinol

Product 1

HCID 229147301-(1-Boc-4-piperidyl)-4-methyl-3,1-benzoxazin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl-(2-(1-Boc-4-piperidinylamino)phenyl) carbinol from Step 2 above (1.9 g, 5.9 mmol) was stirred in dry THF in an ice bath under nitrogen, and triphosgene (0.59 g, 1.98 mmol) was added followed by triethylamine (2.5 ml, 1.8 g, 17.8 mmol). The ice bath was removed and the mixture was stirred at ambient temperature for 18 hours. Water was added, and the mixture was extracted with ethyl acetate. The combined ethyl acetate fractions were washed with 1N HCl followed by saturated sodium bicarbonate, dried over sodium sulfate, filtered, and evaporated to dryness in vacuo to give 1-(1-Boc-4-piperidyl)-4-methyl-3,1-benzoxazin-2-one.

Workup

  1. customThe ice bath was removed
  2. additionWater was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe combined ethyl acetate fractions were washed with 1N HCl
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-d989e2658035412292a542abcaa9345a
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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