Acetic Acid → 5-Methyl-2-furylmethylamine

HRID 1170181Notes

Reaction equation

HRID 1170181 reaction equation
[NH2:1][CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([NH:13][CH2:14][C:15]1[O:16][C:17]([CH3:20])=[CH:18][CH:19]=1)=[N:8]2.[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1.C(O)(=O)C>ClC(Cl)C>[CH3:20][C:17]1[O:16][C:15]([CH2:14][NH2:13])=[CH:19][CH:18]=1.[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH:1][CH2:2][C:3]2[CH:12]=[CH:11][CH:10]=[C:9]3[C:4]=2[CH:5]=[CH:6][C:7]([NH:13][CH2:14][C:15]2[O:16][C:17]([CH3:20])=[CH:18][CH:19]=2)=[N:8]3)=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 680234-FluorobenzaldehydeHCID 68437142HCID 68437142, compound

Product 2

HCID 27246835-Methyl-2-furylmethylamineYield 66%HCID 24991199HCID 24991199, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of (5-aminomethyl-quinolin-2-yl)-(5-methyl-furan-2-ylmethyl)-amine (example 126, step B) (95 mg, 0.355 mmol), 4-fluorobenzaldehyde (97 mg, 0.78 mmol) and acetic acid (85.4 mg, 1.42 mmol) in 1,1-dichloroethane (5 ml) was stirred at room temperature for 30 min. Afterwards sodium triacetoxy-boron hydride (176 mg, 0.75 mmol) was added, the reaction mixture was allowed to stir for 21 h at room temperature, poured into ice/saturated NaHCO3 solution (20 ml) and extracted with ethyl acetate (2×30 ml). The combined organic layers were washed with brine (20 ml), dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel to yield beside 5-{[bis-(4-fluoro-benzyl)-amino]-methyl}-quinolin-2-yl)-(5-methyl-furan-2-ylmethyl)-amine (114 mg, 66%) the title compound as light yellow oil (30 mg, 22%).

Workup

  1. extractionextracted with ethyl acetate (2×30 ml)
  2. washThe combined organic layers were washed with brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel

Sources & evidence

ORD record
ord-51094cc0f2584a4ea327aaa094703c3f
Source dataset
uspto-grants-2010_11
Patent number
US07825253B2

Reaction notes

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