3-(Chloromethyl)pyridine hydrochloride → HCID 54149768, compound

HRID 843161Notes

Reaction equation

HRID 843161 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][CH2:19][NH:20][CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].Cl.Cl[CH2:29][C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1.C(N(CC)C(C)C)(C)C>C(O)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][CH2:19][NH:20][CH:21]3[CH2:26][CH2:25][N:24]([CH2:29][C:30]4[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=4)[CH2:23][CH2:22]3)[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 81531DiisopropylethylamineHCID 53749246HCID 53749246, compound

Product 1

HCID 54149768HCID 54149768, compoundYield 42.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-methyl-4-[3-(piperidin-4-ylamino)-propoxy]-benzofuran-2-carboxylic acid ethyl ester (15 mg), 3-(chloromethyl)pyridine hydrochloride (8 mg) and N,N-diisopropylethylamine (22 μl) in ethanol (1.5 ml) was stirred overnight at 70° C. The reaction mixture was dissolved in ethyl acetate and washed with saturated ammonium chloride solution and water. The organic solvent was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by silica gel column chromatography (dichloromethane-MeOH) to afford 3-methyl-4-[3-(1-pyridin-3-ylmethyl-piperidin-4-ylamino)-propoxy]-benzofuran-2-carboxylic acid ethyl ester (8 mg) as a colorless oil. FAB-MS: m/z 452 (MH+); 1H-NMR (CDCl3): δ 1.43 (3H, t, J=7 Hz), 1.60 (2H, m), 2.00 (4H, m), 2.20 (2H, quintet, J=6.5 Hz), 2.70 (1H, m), 2.72 (3H, s), 2.86 (2H, br d, J=12 Hz), 2.99 (2H, t, J=7 Hz), 3.49 (2H, s), 4.15 (2H, t, J=6 Hz), 4.43 (2H, q, J=7 Hz), 6.59 (1H, d, J=8 Hz), 7.11 (1H, d, J328 Hz), 7.22 (1H, m), 7.29 (1H, t, J=8 Hz), 7.66 (1H, brd, J=8 Hz), 8.48 (1H, m), 8.51 (1H, br s).

Workup

  1. washwashed with saturated ammonium chloride solution and water
  2. dry with materialThe organic solvent was dried over anhydrous sodium sulfate
  3. customevaporated to dryness
  4. customThe residue was purified by silica gel column chromatography (dichloromethane-MeOH)

Sources & evidence

ORD record
ord-283f08064b3b4b96a476235656bdf5f1
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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