Water → N-Trifluoroacetyl-8-chloro-7-fluoro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 1010792Notes

Reaction equation

HRID 1010792 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4].[B-](F)(F)(F)[F:21].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.FC(F)(F)S(O)(=O)=O.O>ClCCCl>[F:19][C:2]([F:18])([F:1])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Cl:17])[C:15]([F:21])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 62406Trifluoromethanesulfonic acidHCID 2724933SelectfluorHCID 22292806N-trifluoroacetyl-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 22292798N-Trifluoroacetyl-8-chloro-7-fluoro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepineYield 60.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of N-trifluoroacetyl-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (2.5 g, 8.5 mmol) in 1,2-dichloroethane (15 mL) was treated with Selectfluor (3.9 g, 11 mmol), trifluoromethanesulfonic acid (8 mL, 90 mmol) and stirred 60 hours at 75 C. The product mixture was poured into water (200 mL), extracted with EtOAc (200 mL), the organic phase washed with saturated aqueous NaHCO3 (2×100 mL), brine (100 mL), dried with Na2SO4 and concentrated. The crude product was purified by flash chromatography (6% EtOAc in hexane, silica) resulting in 1.6 g of a white solid. MS calculated for C13H12ClF4NO+H: 310, observed: 310.

Workup

  1. extractionextracted with EtOAc (200 mL)
  2. washthe organic phase washed with saturated aqueous NaHCO3 (2×100 mL), brine (100 mL)
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography (6% EtOAc in hexane, silica)

Sources & evidence

ORD record
ord-4eb48827670741009bce72963200c742
Source dataset
uspto-grants-2011_07
Patent number
US07977329B2

Reaction notes

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