p-Fluorophenethylamine → HCID 11171758, compound

HRID 896568Notes

Reaction equation

HRID 896568 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH2:8])=[CH:4][CH:3]=1.[C:11]([CH2:13][C:14](OCC)=[O:15])#[N:12]>>[C:11]([CH2:13][C:14]([NH:8][CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=1)=[O:15])#[N:12]

Participants

3

Reactant 2

HCID 4653p-FluorophenethylamineHCID 7764Ethyl cyanoacetate

Product 1

HCID 11171758HCID 11171758, compound

Conditions

Temperature
100 °C

Procedure

A mixture of 4-fluorophenethylamine (10.6 g, 76.2 mmol) and ethyl cyanoacetate (8.09 mL, 76.2 mmol) was heated in an open flask at 100° C. for 18 hours. The mixture was cooled and the resulting solid was triturated with ethanol, filtered and dried. Recrystallization from ethanol provided off-white crystals (8.2 g, 52%). 1H NMR (300 MHz, CDCl3) δ7.17 (m, 2H), 7.03 (t, J=9 Hz, 2H), 6.26 (bs, 1H), 3.54 (q, J=7 Hz, 2H), 3.35 (s, 2H), 2.84 (t, J=7 Hz, 2H). Mass spec (ES−) m/z 205.2 (M−H−, 100%).

Workup

  1. temperatureThe mixture was cooled
  2. customthe resulting solid was triturated with ethanol
  3. filtrationfiltered
  4. customdried
  5. customRecrystallization from ethanol provided off-white crystals (8.2 g, 52%)

Sources & evidence

ORD record
ord-57c33bbf41304769ae5ca6f5e33a1e45
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

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