Triethylamine → Acetamide, N-(6-aminohexyl)-2,2,2-trifluoro-

HRID 1736626Notes

Reaction equation

HRID 1736626 reaction equation
C(O[C:4](=[O:9])[C:5]([F:8])([F:7])[F:6])C.[CH:10]([NH2:17])(N)[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C([N:20](CC)CC)C>CO>[C:5]([C:4]([NH:20][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][NH2:17])=[O:9])([F:6])([F:7])[F:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9794Ethyl trifluoroacetateHCID 134940Hexanediamine

Product 1

HCID 11805999Acetamide, N-(6-aminohexyl)-2,2,2-trifluoro-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-1-trifluoroacetylhexanediamine, (CF3CONH(CH2)6NH2) is prepared by adding ethyltrifluoroacetate (1.2 ml, 10 mmol) dropwise over one hour to a stirred mixture of hexanediamine (1.16 g; 10 mmol) and triethylamine (1 ml; 7 mmol) in 20 ml methanol. The solution is stirred overnight. After removal of solvents, the reaction mixture is flash chromatographed on silica using 0-25% methanol in dichloromethane. The fractions containing the desired product are pooled and concentrated to give a colorless powder (1.1 gm, yield-42.6%); melting point 52° C; 1H NMR (CDCl3, d, TMS=) .00) 7.1-7.2 (m, 3H, NH2, NH) 3.2-3.3 (m, 2H, CO--NH--CH2), 2.8-2.9 (m 2 H, CH2 --NH2) 1.2-1.6 (m, 8H,--CH--(CH2)2 --CH2 --).

Workup

  1. customAfter removal of solvents
  2. customchromatographed on silica using 0-25% methanol in dichloromethane
  3. additionThe fractions containing the desired product
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f1e4c973303445b7afa6d996818325e9
Source dataset
uspto-grants-1996_07
Patent number
US05541306

Reaction notes

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