Triethylamine → 1-(4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)-2,2,2-trifluoroethanone

HRID 710487Notes

Reaction equation

HRID 710487 reaction equation
[CH2:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][NH:3][CH2:2]1.CCN(CC)CC.[O:19](C(C(F)(F)F)=O)[C:20]([C:22]([F:25])([F:24])[F:23])=O>C(Cl)Cl>[F:23][C:22]([F:25])([F:24])[C:20]([N:3]1[CH2:2][CH2:1][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4]1)=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 14002432,3,4,5-Tetrahydro-1H-benzo(d)azepine

Product 1

HCID 218871391-(4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)-2,2,2-trifluoroethanoneYield 101.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.25 g, 1.7 mmol) in anhydrous CH2Cl2 (5 ml), Et3N (0.28 ml, 2 mmol) was added at 0° C. and under N2, followed by (CF3CO)2O (0.29 ml, 2 mmol) and the resulting mixture was stirred for 1 h, than washed with aqueous NaHCO3 and H2O. The organic layer was dried over MgSO4, filtered and the filtrate was evaporated to dryness to give the title product (0.418 g, 100%), as pale oil. 1H-NMR (CDCl3) 3.6-3.97 (m, 8H); 7.11-7.19 (m, 4H).

Workup

  1. washthan washed with aqueous NaHCO3 and H2O
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-7cd3c541c1d44bb886532d7f0a090c41
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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