4-Dodecylaniline → HCID 19980610, compound

HRID 2248406Notes

Reaction equation

HRID 2248406 reaction equation
[CH2:1]([C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Cl:20][CH2:21][CH2:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)=[O:24].C(N(CC)CC)C>C(OCC)C>[ClH:20].[CH2:1]([C:13]1[CH:14]=[CH:15][C:16]([NH:17][CH2:21][CH2:22][C:23]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)=[O:24])=[CH:18][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 77014-DodecylanilineHCID 8471TriethylamineHCID 676722-Chloro-4'-fluoropropiophenone

Product 1

HCID 19980610HCID 19980610, compoundYield 8.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-dodecylaniline (26.2 g, 0.1 mole) and 3-chloro-4'-fluoropropiophenone (18.7 g, 0.1 mole) in diethyl ether (200 ml) was stirred for 16 hours at room temperature. The mixture was treated with triethylamine (10.1 g, 0.1 mole), stirred for an additional 72 hours, and concentrated in vacuo. The residue was partitioned between diethyl ether (200 ml) and hydrochloric acid (IN, 200 ml). The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to an impure tacky solid (41.9 g). A small portion (5 g) was recrystallized from ethanol to give the title compound (4.0 g); mp 107°-109° C.; IR(nujol) C=O @ 1674 cm-1 ; NMR(DMSO-d6, TMS): δ0.5-1.7(m,23H,C11H23), 2.50(t,2H,ArCH2), 3.30(m,4H, N--CH2 --CH2), 6.50,7.00(2d,4H,p-N-phenyl), [ 7.37(d of d,2H) and 8.07(m,2H) p-F-phenyl]; Anal. Calcd. for C27H38FNO.HCl, MW 448.05: C,73.37; H,8.77; N,3.19. Found: C,73.09; H,8.50; N,3.19. Mass spectrum m/e 411,284.

Workup

  1. stirringstirred for an additional 72 hours
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between diethyl ether (200 ml) and hydrochloric acid (IN, 200 ml)
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to an impure tacky solid (41.9 g)
  8. customA small portion (5 g) was recrystallized from ethanol

Sources & evidence

ORD record
ord-4537a3bd1850494baeb3073387362c80
Source dataset
uspto-grants-1991_08
Patent number
US05039706

Reaction notes

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