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

HRID 2122147Notes

Reaction equation

HRID 2122147 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-4c80a3929d3d401abd9ac6b9bb9db72f
Source dataset
uspto-grants-2004_02
Patent number
US06696435B2

Reaction notes

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