Acetyl chloride → trans-4-acetyl-10-phenylmethoxy-3,4,4a,5,6,11b-hexahydro-2H-[1]benzoxepino[5,4-b]-1,4-oxazine

HRID 35361Notes

Reaction equation

HRID 35361 reaction equation
Cl.[C:2]1([CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]3[O:24][CH2:23][CH2:22][C@@H:21]4[C@H:16]([O:17][CH2:18][CH2:19][NH:20]4)[C:14]=3[CH:15]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:32](Cl)(=[O:34])[CH3:33]>C(Cl)Cl>[C:32]([N:20]1[CH2:19][CH2:18][O:17][C@@H:16]2[C:14]3[CH:15]=[C:10]([O:9][CH2:8][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:11]=[CH:12][C:13]=3[O:24][CH2:23][CH2:22][C@@H:21]12)(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 70404222HCID 70404222, compound

Product 1

HCID 54388109trans-4-acetyl-10-phenylmethoxy-3,4,4a,5,6,11b-hexahydro-2H-[1]benzoxepino[5,4-b]-1,4-oxazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3.47 g of trans-10-phenylmethoxy-3,4,4a,5,6,11b-hexahydro-2H-[1]benzoxepino[5,4-b]-1,4-oxazine hydrochloride, 50 ml of triethylamine and 25 ml of methylene chloride is cooled in ice and 1.0 ml of acetyl chloride dissolved in 25 ml of methylene chloride is added dropwise thereto. The solution is stirred overnight at room temperature, washed with a dilute hydrochloric acid solution and dried over anhydrous magnesium sulfate. The drying agent is removed via filtration and the filtrate evaporated to yield trans-4-acetyl-10-phenylmethoxy-3,4,4a,5,6,11b-hexahydro-2H-[1]benzoxepino[5,4-b]-1,4-oxazine as an oil.

Workup

  1. temperatureis cooled in ice
  2. additionis added dropwise
  3. washwashed with a dilute hydrochloric acid solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe drying agent is removed via filtration
  6. customthe filtrate evaporated

Sources & evidence

ORD record
ord-f67a9c000ad04243bcb2e13ef47ddf7b
Source dataset
uspto-grants-1988_08
Patent number
US04766212

Reaction notes

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