Acetic Acid → N-{4-[(4-butylphenyl)ethynyl]benzyl)-1-hexanamine

HRID 551918Notes

Reaction equation

HRID 551918 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH2:21]([NH2:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:20]=[CH:19][C:16]([CH2:17][NH:27][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8102HexylamineHCID 5049666Sodium triacetoxyborohydrideHCID 113345124-[2-(4-Butylphenyl)ethynyl]benzaldehyde

Product 1

HCID 57554478N-{4-[(4-butylphenyl)ethynyl]benzyl)-1-hexanamineYield 32.6%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[(4-butylphenyl)ethynyl]benzaldehyde (334 mg, 1.27 mmol, intermediate which may be obtained according to methods disclosed in EP03103780.7) and hexylamine (Aldrich, 98 μL, 1.53 mmol) in DCE (15.00 mL) was added acetic acid (110 mL) and sodium triacetoxyborohydride (405 mg, 1.91 mmol) and the resulting mixture was stirred at rt for 3 hrs. The reaction mixture was then diluted with DCM and washed with a saturated aqueous solution of NaHCO3 and brine. The organic layer was dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was purified by flash chromatography on silicagel (DCM, DCM/MeOH/NH4OH 98:2:1 then 95:5:1) to give 144 mg (32%) of the title compound. HPLC, Rt: 4.59 min (purity: 98.7%). 1H NMR (CD3Cl3) δ: 0.87 (t, J=6.9 Hz, 3H), 0.91 (t, J=7.3 Hz, 3H), 1.28-1.64 (m, 13H), 2.6 (t, J=7.3 Hz, 4H), 3.78 (s, 2H), 7.14 (d, J=8.1 Hz, 2H), 7.28 (d, J=8.3 Hz, 2H), 7.42 (d, J=8.3 Hz, 2H), 7.47 (d, J=8.1 Hz, 2H).

Workup

  1. washwashed with a saturated aqueous solution of NaHCO3 and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. customthe solvents were removed under reduced pressure
  4. customThe crude product was purified by flash chromatography on silicagel (DCM, DCM/MeOH/NH4OH 98:2:1

Sources & evidence

ORD record
ord-61ba917d14f044babe7825b6345be49e
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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