N-Allyl-2,2,2-trifluoroacetamide → HCID 86637611, compound

HRID 74330Notes

Reaction equation

HRID 74330 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[O:5][CH2:6][CH:7]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[CH2:17]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH:18]=[CH2:19]>>[CH:7]1([CH2:6][O:5][C:4]2[CH:3]=[C:2](/[CH:19]=[CH:18]/[CH2:17][NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH:16]=[CH:15][CH:14]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

3

Reactant 2

HCID 558569N-Allyl-2,2,2-trifluoroacetamideHCID 67317652((3-Bromophenoxy)methyl)cycloheptane

Product 1

HCID 86637611HCID 86637611, compound

Procedure

((3-Bromophenoxy)methyl)cycloheptane was coupled with N-allyl-2,2,2-trifluoroacetamide following the method used in Example 10 except that the mixture was heated for 23 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure and partitioned between EtOAc and water. The combined organics were washed with water and brine, dried over MgSO4 and concentrated under reduced pressure. Purification by flash chromatography (10% EtOAc-hexanes) gave (E)-N-(3-(3-(cycloheptylmethoxy)phenyl)allyl)-2,2,2-trifluoroacetamide. Yield (0.7015 g, 52%): 1H NMR (400 MHz, CDCl3) δ 7.23 (t, J=7.6 Hz, 1H), 6.90-6.94 (m, 2H), 6.81 (dd, J=8.4, 1.6 Hz, 1H), 6.56 (d, J=15.6 Hz, 1H), 6.39 (br s, 1H), 6.12-6.19 (m, 1H), 4.13 (t, J=6.0 Hz, 2H), 3.73 (d, J=9.6 Hz, 2H), 1.92-2.10 (m, 1H), 1.82-1.90 (m, 2H), 1.42-1.76 (m, 8H), 1.24-1.36 (m, 2H).

Workup

  1. temperaturewas heated for 23 h
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. custompartitioned between EtOAc and water
  4. washThe combined organics were washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography (10% EtOAc-hexanes)

Sources & evidence

ORD record
ord-e7e617260d894de7be52ffc69d7a144c
Source dataset
uspto-grants-2014_09
Patent number
US08829244B2

Reaction notes

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