Triethylamine → 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

HRID 16149Notes

Reaction equation

HRID 16149 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.C(N(CC)CC)C.[Cl:17][C:18]1[CH:37]=[CH:36][C:21]2[O:22][C:23]3[CH:35]=[CH:34][CH:33]=[CH:32][C:24]=3[C@@H:25]3[C@H:30]([NH2:31])[CH2:29][CH2:28][CH2:27][N:26]3[C:20]=2[CH:19]=1>CO>[Cl:17][C:18]1[CH:37]=[CH:36][C:21]2[O:22][C:23]3[CH:35]=[CH:34][CH:33]=[CH:32][C:24]=3[C@@H:25]3[C@H:30]([NH:31][C:3](=[O:5])[C:2]([F:1])([F:8])[F:9])[CH2:29][CH2:28][CH2:27][N:26]3[C:20]=2[CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9794Ethyl trifluoroacetateHCID 70883458trans-7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine

Product 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-trifluoroacetamideYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Successively, ethyl trifluoroacetate (1.41 mL, 11.8 mmol) and triethylamine (628 μL, 4.5 mmol) were added to trans-7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine (291 mg, 0.97 mmol) in 11.8 mL of methanol. The resulting mixture was heated to 50° C. for 18 h. A precipitate was formed. The mixture was evaporated under reduced pressure to remove volatile reagents and 5 mL of methanol was added. After 30 min. stirring the precipitate was filtered off, washed with diethyl ether and dried to give 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 as an off-white solid (330 mg, 86%). Data: 1H-NMR (400 MHz, CDCl3) 1.85 (m, 2H), 2.26 (m, 1H), 3.12 (m, 1H), 3.20 (m, 1H), 3.62 (dt, J=12.0, 4.0, 1H), 4.38 (d, J=8.0, 1H), 4.68 (m, 1H), 6.76 (dd, J=8.0, 3.0, 1H), 6.93 (d, J=3.0, 1H), 7.04 (d, J=8.0, 1H), 7.08 (dt, J=8.0, 2.0, 1H), 7.17 (dd, J=8.0, 2.0, 2H), 7.29 (dt, J=8.0, 2.0, 1H). (m/z)=397 (M+H)+.

Workup

  1. customA precipitate was formed
  2. customThe mixture was evaporated under reduced pressure
  3. customto remove volatile reagents and 5 mL of methanol
  4. additionwas added
  5. filtrationwas filtered off
  6. washwashed with diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-031d11eb0cfb4457bee11cc748affea5
Source dataset
uspto-grants-2010_06
Patent number
US07737136B2

Reaction notes

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