Acetonitrile → HCID 87283348, compound

HRID 1869707Notes

Reaction equation

HRID 1869707 reaction equation
[CH2:1]([NH2:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].C(#N)C.[CH2:14]=[C:15]([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17]>O>[CH2:1]([NH:10][CH2:14][CH:15]([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 16215NonylamineHCID 914503,3,3-Trifluoro-2-(trifluoromethyl)-1-propene3×

Product 1

HCID 87283348HCID 87283348, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of nonylamine (7.5 g) and acetonitrile (10 mL) was added HFIB in several portions over a period of about 0.5 h until a gentle reflux of HFIB was observed which did not dissipate. A dry-ice condenser was used to obtain the gentle reflux of HFIB at 25° C. for 15 h. The reaction mixture was poured into water (150 mL) and the bottom layer separated, and washed with water to provide N-nonyl N-(2-trifluoromethyl-3,3,3-trifluoropropyl)amine (13.5 g): 1H NMR (CDCl3) 0.88 (t, J=7 Hz, 3H), 1.28 (m, 12H), 1.47 (quintet, J=7 Hz, 2H), 2.62 (t, J=7 Hz, 2H), 3.09 (m, 3H) ppm; 19F NMR (CDCl3) −67.0 (d, J=8 Hz) ppm; MS (m/e) 307 (M+, 2.5%), 292 (0.2%), 278 (0.3%), 264 (0.5%), 250 (0.8%), 236 (0.5%), 208 (2.6%),194 (100%),156 (5.9%).

Workup

  1. customA dry-ice condenser was used
  2. customto obtain the
  3. customthe bottom layer separated
  4. washwashed with water

Sources & evidence

ORD record
ord-7914f8010f244f169d3c867d8449616c
Source dataset
uspto-grants-2009_12
Patent number
US07638650B2

Reaction notes

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