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

HRID 1884652Notes

Reaction equation

HRID 1884652 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-b95b7f369aac414ba5d7a9cbf4d3abbf
Source dataset
uspto-grants-2004_07
Patent number
US06765023B2

Reaction notes

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