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

HRID 1839986Notes

Reaction equation

HRID 1839986 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) δ 7.37 (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-e55fb445b9e64f22aec8da310e73a0c6
Source dataset
uspto-grants-2004_01
Patent number
US06677382B1

Reaction notes

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