Hydrochloric Acid → trans-N-(8-bromo-7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide

HRID 16163Notes

Reaction equation

HRID 16163 reaction equation
[Br: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.C(OCC)(=O)C>[Br:1][C:36]1[C:11]([Cl:10])=[CH:12][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]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 67184N-bromobutanimideHCID 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 1

HCID 86599872trans-N-(8-bromo-7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamideYield 130.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-bromosuccinimide (9.2 mg, 0.05 mmol) and 0.5 μL of 1N HCl were 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 512 μL of acetone. The resulting mixture was stirred at room temperature for 30 min. The mixture was diluted with ethyl acetate, washed with saturated aq. sodium bicarbonate and water, dried (Na2SO4) and evaporated to give trans-N-(8-bromo-7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide as a white solid (31 mg, 100%). Data: 1H-NMR (400 MHz, CDCl3) 1.85 (m, 4H), 2.27 (m, 2H), 3.20 (m, 1H), 3.64 (m, 1H), 4.44 (d, J=8.0, 1H), 4.65 (m, 1H), 6.26 (b, 1H), 7.02 (s, 1H), 7.10 (dt, J=8.0, 2.0, 1H), 7.16 (m, 2H), 7.30 (dt, J=8.0, 3.0, 1H), 7.35 (s, 1H). (m/z)=477 (M+H)+.

Workup

  1. washwashed with saturated aq. sodium bicarbonate and water
  2. dry with materialdried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-cd56712d44b14c6dbd87b05fdf7e6384
Source dataset
uspto-grants-2010_06
Patent number
US07737136B2

Reaction notes

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