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

HRID 16164Notes

Reaction equation

HRID 16164 reaction equation
Cl[C:2]1[CH:27]=[CH:26][C:5]2[O:6][C:7]3[CH:25]=[CH:24][CH:23]=[CH:22][C:8]=3[C@@H:9]3[C@H:14]([NH:15][C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[CH2:13][CH2:12][CH2:11][N:10]3[C:4]=2[CH:3]=1>CN(C=O)C.[Pd]>[C@H:14]1([NH:15][C:16](=[O:21])[C:17]([F:20])([F:18])[F:19])[C@@H:9]2[N:10]([C:4]3[CH:3]=[CH:2][CH:27]=[CH:26][C:5]=3[O:6][C:7]3[CH:25]=[CH:24][CH:23]=[CH:22][C:8]=32)[CH2:11][CH2:12][CH2:13]1

Participants

4

Reactant 1

HCID 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 86599873trans-N-(2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamideYield 98.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

10 mg Pd/C 10% was added to a solution of 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 (100 mg, 0.25 mmol) in 5 mL of DMF. The suspension was shaken under H2 atmosphere for 2 days. The mixture was filtered, poured into water and extracted with diethyl ether. The organic layer was washed with water, dried (Na2SO4) and evaporated to give trans-N-(2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide (89 mg, 98%). Data: 1H-NMR (400 MHz, CDCl3) 1.85 (m, 3H), 2.99 (m, 1H), 3.18 (m, 1H), 3.75 (m, 1H), 4.50 (d, J=8,1H), 4.72 (m, 1H), 6.62 (br, 1H), 6.84-7.30 (8 arH). (m/z)=362 (M+H)+.

Workup

  1. filtrationThe mixture was filtered
  2. additionpoured into water
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-3a0fbadf15ca47b79d2f9ce10e431c39
Source dataset
uspto-grants-2010_06
Patent number
US07737136B2

Reaction notes

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