Acetic Acid → N-[(6-Bromopyridin-2-yl)methyl]-2,6-bis(1-ethylpropyl)aniline

HRID 634063Notes

Reaction equation

HRID 634063 reaction equation
[Br:1][C:2]1[N:7]=[C:6](/[CH:8]=[N:9]/[C:10]2[C:15]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:14][CH:13]=[CH:12][C:11]=2[CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[CH:5]=[CH:4][CH:3]=1.[BH3-]C#N.[Na+].CC(O)=O.CO>O>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][NH:9][C:10]2[C:15]([CH:16]([CH2:17][CH3:18])[CH2:19][CH3:20])=[CH:14][CH:13]=[CH:12][C:11]=2[CH:21]([CH2:22][CH3:23])[CH2:24][CH3:25])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 178442119HCID 178442119, compound

Product 1

HCID 117652978N-[(6-Bromopyridin-2-yl)methyl]-2,6-bis(1-ethylpropyl)aniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In argon atmosphere, a mixture of 11.2 g (28 mmol) of N-[(1E)-(6-bromopyridin-2-yl)methylene]-2,6-bis(1-ethylpropyl)aniline, 2.80 g (45 mmol) of NaBH3CN, 1 ml of AcOH and 230 ml of methanol was refluxed for 12 h. The obtained mixture was cooled, poured into 300 ml of water, and then crude product was extracted with 3×200 ml of ethyl acetate. The combined extract was dried over Na2SO4 and evaporated to dryness. Yield 10.3 g (93%) of yellow oil. Anal. calc. for C23H31BrN2: C, 65.50; H, 7.75; N, 6.94. Found: C, 65.36; H, 7.69; N, 6.82. 1H NMR (CDCl3): δ 7.52 (m, 1H, 4-H in Py), 7.41 (m, 1H, 3-H in Py), 7.38 (m, 1H, 5-H in Py), 7.03-7.08 (m, 1H, 4-H in dipentylphenyl), 6.97-6.99 (m, 2H, 3, 5-H in dipentylphenyl), 4.10 (s, 2H, CH2NH), 3.73 (br.s, 1H, NH), 2.86 (m, 2H, CHEt2), 1.70 (m, 4H, CH2Me), 1.49 (m, 4H, CH2Me), 0.79 (t, J=7.3 Hz, 12H, CH2Me).

Workup

  1. temperaturewas refluxed for 12 h
  2. temperatureThe obtained mixture was cooled
  3. extractioncrude product was extracted with 3×200 ml of ethyl acetate
  4. extractionThe combined extract
  5. dry with materialwas dried over Na2SO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-f7b963023d044417b08d6e67dbee4a56
Source dataset
uspto-grants-2016_04
Patent number
US09321858B2

Reaction notes

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