1,3-Propanediamine → HCID 87283278, compound

HRID 1869708Notes

Reaction equation

HRID 1869708 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH2:5].CO.[CH2:8]=[C:9]([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11]>O>[F:11][C:10]([F:13])([F:12])[CH:9]([C:14]([F:17])([F:16])[F:15])[CH2:8][NH:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:8][CH:9]([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11]

Participants

5

Reactant 3

HCID 4281,3-PropanediamineHCID 887MethanolHCID 914503,3,3-Trifluoro-2-(trifluoromethyl)-1-propene3×

Product 1

HCID 87283278HCID 87283278, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1,3-diaminopropane (3.5 g) and methanol (4 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 20° C. for 15 h. The mixture was poured into water (100 mL) and the bottom layer washed with water to provide 1,3-di-(2-trifluoromethyl-3,3,3-trifluoropropylamino)propane (13 g): MS (m/e) 402 (M+, 0.5%), 251 (12%), 221 (82%), 208 (23%),194 (100%); 1H NMR (CDCl3): 1.66 (quintet, J=6.5 Hz, 2H), 2.72 (t, J=6.5 Hz, 4H), 3.08 (m, 6H) ppm.

Workup

  1. customA dry-ice condenser was used
  2. customto obtain the
  3. washthe bottom layer washed with water

Sources & evidence

ORD record
ord-300bdb42d9e8450f8c1da8ba65d415d4
Source dataset
uspto-grants-2009_12
Patent number
US07638650B2

Reaction notes

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