Hydrochloric Acid → 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

HRID 16162Notes

Reaction equation

HRID 16162 reaction equation
[Cl:1]N1C(=O)CCC1=O.Cl.[Cl:10][C:11]1[CH:36]=[CH:35][C:14]2[O:15][C:16]3[CH:34]=[CH:33][CH:32]=[CH:31][C:17]=3[C@@H:18]3[C@H:23]([NH:24][C:25](=[O:30])[C:26]([F:29])([F:28])[F:27])[CH2:22][CH2:21][CH2:20][N:19]3[C:13]=2[CH:12]=1>CC(C)=O>[Cl:1][C:12]1[C:13]2[N:19]3[CH2:20][CH2:21][CH2:22][C@@H:23]([NH:24][C:25](=[O:30])[C:26]([F:29])([F:28])[F:27])[C@H:18]3[C:17]3[CH:31]=[CH:32][CH:33]=[CH:34][C:16]=3[O:15][C:14]=2[CH:35]=[CH:36][C:11]=1[Cl:10].[Cl:10][C:11]1[C:36]([Cl:1])=[CH:35][C:14]2[O:15][C:16]3[CH:34]=[CH:33][CH:32]=[CH:31][C:17]=3[C@@H:18]3[C@H:23]([NH:24][C:25](=[O:30])[C:26]([F:29])([F:28])[F:27])[CH2:22][CH2:21][CH2:20][N:19]3[C:13]=2[CH:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 31398ChlorosuccinimideHCID 86599857trans-N-(7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide

Product 2

HCID 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-trifluoroacetamideYield 17%HCID 86599871trans-N-(7,8-dichloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamideYield 7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-chlorosuccinimide (6.87 mg, 0.05 mmol) and 0.5 μL 1N HCl was added to trans-N-(7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide (20 mg, 0.05 mmol) in 102 μL of acetone. The resulting mixture was stirred at room temperature for 18 h. No reaction was observed. The reaction was repeated under the same conditions. The resulting mixture was stirred at room temperature for 1.5 h. The organic layer was washed with saturated aq. sodium bicarbonate and water, dried (Na2SO4) and evaporated and the crude compound was purified by preparative HPLC to give 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 (3.6 mg, 17%) and trans-N-(7,8-dichloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide (1.6 mg, 7%). Data: (m/z)=431 (M+H)+.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 1.5 h
  2. washThe organic layer was washed with saturated aq. sodium bicarbonate and water
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customthe crude compound was purified by preparative HPLC

Sources & evidence

ORD record
ord-70558b28549a49b094a73049aec419d4
Source dataset
uspto-grants-2010_06
Patent number
US07737136B2

Reaction notes

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