Benzylamine → HCID 22675951, compound

HRID 1005992Notes

Reaction equation

HRID 1005992 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]([F:15])([F:14])[CH:11]1[O:13][CH2:12]1>>[C:2]1([CH2:1][N:8]([CH2:12][CH:11]([OH:13])[C:10]([F:15])([F:14])[F:9])[CH2:12][CH:11]([OH:13])[C:10]([F:15])([F:14])[F:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 5207692-(Trifluoromethyl)oxirane

Product 1

HCID 22675951HCID 22675951, compoundYield 57.8%

Conditions

Temperature
80 °C

Procedure

Benzylamine (1.5 eq, 2.88 g, 2.94 mL, 26.8 mmol) was combined with 3,3,3-trifluoro-1,2-epoxypropane (2.0 g, 17.86 mmol) in a sealed glass tube and heated at 80° C. for 18 h. Upon cooling to room temperature, the reaction mixture formed a slushy white solid. The solid was collected by filtration and washed with diethyl ether. The mother liquor was concentrated in vacuo to give 1.71 g (43%) of the desired 1,1′-[(phenyl-methyl)imino]bis[3,3,3-trifluoro-2-propanol] product as a colorless oil. FABMS m/z=332 [M+H]+. 1H NMR (CDCl3) δ 2.85-2.96 (m, 4H), 3.94 (s, 2H), 3.94-3.97 (m, 2H), 7.24-7.37 (m, 5H).

Workup

  1. temperatureUpon cooling to room temperature
  2. customthe reaction mixture formed a slushy white solid
  3. filtrationThe solid was collected by filtration
  4. washwashed with diethyl ether
  5. concentrationThe mother liquor was concentrated in vacuo

Sources & evidence

ORD record
ord-78f7fc2b780347c2b6011577cb516a4b
Source dataset
uspto-grants-2004_09
Patent number
US06787570B2

Reaction notes

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