3-(Trifluoromethoxy)benzylamine → 3-[[[3-(Trifluoromethoxy)phenyl]methyl]amino]-1,1,1-trifluoro-2-propanol

HRID 1017080Notes

Reaction equation

HRID 1017080 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:5]=[C:6]([CH2:10][NH2:11])[CH:7]=[CH:8][CH:9]=1.[F:14][C:15]([F:20])([F:19])[CH:16]1[O:18][CH2:17]1>>[F:1][C:2]([F:12])([F:13])[O:3][C:4]1[CH:5]=[C:6]([CH2:10][NH:11][CH2:17][CH:16]([OH:18])[C:15]([F:20])([F:19])[F:14])[CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 1452643-(Trifluoromethoxy)benzylamineHCID 5207692-(Trifluoromethyl)oxirane

Product 1

HCID 219187773-[[[3-(Trifluoromethoxy)phenyl]methyl]amino]-1,1,1-trifluoro-2-propanolYield 37%

Conditions

Temperature
80 °C

Procedure

EX-632A) 3-Trifluoromethoxybenzenemethanamine (1.15 g, 6 mmol) and 1,1,1-trifluoro-2,3-epoxypropane (0.67 g, 6 mmol) were combined and stirred at 80° C. for 1.5 h. The mixture was cooled to room temperature, and the resulting solid was recrystallized from hot hexanes. The white solid was isolated by vacuum filtration and washed with cold hexanes to give 0.67 g (37%) of pure 3-[[[3-(trifluoromethoxy)-phenyl]methyl]amino]-1,1,1-trifluoro-2-propanol. 1H NMR (CDCl3) δ7.37 (t, 1H), 7.24 (d, 1H), 7.15 (m, 2H), 3.99 (m, 1H), 3.85 (d, 2H), 2.98 (dd, 1H), 2.88 (dd, 1H), 2.79 (s, 1H). 19F NMR (CDCl3) δ−58.19 (s, 3F), −78.88 (s, 3F). HRMS calcd. for C11H11F6NO2: 304.0772 [M+H]+, found: 304.0794.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe resulting solid was recrystallized from hot hexanes
  3. customThe white solid was isolated by vacuum filtration
  4. washwashed with cold hexanes

Sources & evidence

ORD record
ord-53aaeea80e574d3cbe7162b345189e8b
Source dataset
uspto-grants-2002_11
Patent number
US06476075B1

Reaction notes

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