Potassium Carbonate → trans-6,7-Dichloro-2,3,4,14b-tetrahydro-N-(2-methoxyethyl)-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine

HRID 16170Notes

Reaction equation

HRID 16170 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].[Cl:7][C:8]1[C:18]2[N:17]3[CH2:19][CH2:20][CH2:21][C@@H:22]([NH:23][C:24](=O)[C:25](F)(F)F)[C@H:16]3[C:15]3[CH:30]=[CH:31][CH:32]=[CH:33][C:14]=3[O:13][C:12]=2[CH:11]=[CH:10][C:9]=1[Cl:34]>CO.O>[Cl:7][C:8]1[C:18]2[N:17]3[CH2:19][CH2:20][CH2:21][C@@H:22]([NH:23][CH2:24][CH2:25][O:4][CH3:1])[C@H:16]3[C:15]3[CH:30]=[CH:31][CH:32]=[CH:33][C:14]=3[O:13][C:12]=2[CH:11]=[CH:10][C:9]=1[Cl:34]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86599870trans-N-(6,7-dichloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide

Product 1

HCID 86599878trans-6,7-Dichloro-2,3,4,14b-tetrahydro-N-(2-methoxyethyl)-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amineYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

K2CO3 (537 mg, 3.9 mmol) was added to a solution of trans-N-(6,7-dichloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide (322 mg, 0.75 mmol) in methanol (28 mL) and water (1.7 mL). The reaction mixture was stirred at reflux temperature for 2 h whereafter the methanol was removed under reduced pressure. Water was added to the remaining product and the water layer was extracted with CH2Cl2 (3×). The combined organic layers were washed with brine, dried (Na2SO4) and evaporated to give the crude title compound (266 mg, 100%).

Workup

  1. customwas removed under reduced pressure
  2. additionWater was added to the remaining product
  3. extractionthe water layer was extracted with CH2Cl2 (3×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-b6a3f28985694672be061f2771a76dbe
Source dataset
uspto-grants-2010_06
Patent number
US07737136B2

Reaction notes

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