N,N-Dimethylaniline → 2-Amino-4-nonadecylpyridine

HRID 1159739Notes

Reaction equation

HRID 1159739 reaction equation
[CH2:1]([C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[NH2-].[Na+].C[N:29](C)C1C=CC=CC=1>O>[NH2:29][C:24]1[CH:25]=[C:20]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:21]=[CH:22][N:23]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 24533Sodium amideHCID 45203574-Nonadecylpyridine

Product 1

HCID 686447652-Amino-4-nonadecylpyridineYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 0.5 molar portion of 4-nonadecylpyridine, 0.59 mole of sodium amide and 1.18 moles of N,N-dimethylaniline was heated at 150° C. for six hours. The reaction mixture, after cooling, was poured into water, and the dimethylaniline layer was separated and dried over anhydrous potassium carbonate. After removal of the solvent in vacuo the residue was stirred in petroleum ether and crystallized from ethyl acetate/ligroin. Yield 45%. Anal. Calcd for C24H44N2: C, 79.93; H, 12.30; N, 7.77. Found: C, 79.63; H, 12.40; N, 7.60. MS (ESIMS): m/z: 360.4.

Workup

  1. temperatureThe reaction mixture, after cooling
  2. customthe dimethylaniline layer was separated
  3. dry with materialdried over anhydrous potassium carbonate
  4. customAfter removal of the solvent in vacuo the residue
  5. customcrystallized from ethyl acetate/ligroin

Sources & evidence

ORD record
ord-f71c753aafd84fbca5eed29db5194c11
Source dataset
uspto-grants-2010_10
Patent number
US07812251B2

Reaction notes

Loading…