4-Methoxybenzylamine → HCID 61530125, compound

HRID 920858Notes

Reaction equation

HRID 920858 reaction equation
[F:1][C:2]([F:7])([F:6])[CH:3]1[CH2:5][O:4]1.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH2:17])=[CH:12][CH:11]=1>C(O)(C)C>[F:1][C:2]([F:7])([F:6])[CH:3]([OH:4])[CH2:5][NH:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][CH3:8])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 5207692-(Trifluoromethyl)oxirane

Product 1

HCID 61530125HCID 61530125, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(trifluoromethyl)oxirane (2.00 g, 17.8 mmol) in isopropanol (20 mL) in a pressure tube was added (4-methoxyphenyl)methanamine (7.35 g, 53.5 mmol). The reaction vessel was capped and heated at 80° C. for 3 h. The reaction mixture was concentrated and purified by silica gel chromatography (80 g REDISEP® column, eluting with a gradient from 0-60% EtOAc in hexanes). The required fractions were concentrated to obtain Intermediate A125A (3.1 g, 70.6% yield) as a white solid. MS(ES) m/z=287 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 7.29-7.17 (m, 2H), 6.87 (d, J=8.5 Hz, 2H), 6.25 (br. s., 1H), 4.04 (td, J=7.8, 3.3 Hz, 1H), 3.72 (s, 3H), 3.66 (d, J=1.8 Hz, 2H), 2.74-2.55 (m, 2H), 2.08 (br. s., 1H).

Workup

  1. customThe reaction vessel was capped
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by silica gel chromatography (80 g REDISEP® column
  4. washeluting with a gradient from 0-60% EtOAc in hexanes)
  5. concentrationThe required fractions were concentrated
  6. customto obtain Intermediate A125A (3.1 g, 70.6% yield) as a white solid

Sources & evidence

ORD record
ord-6390be97b4c94819b03af457df78bffc
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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