Piperidine → 7-Methyl-2-[2-methyl-4-(3-piperidin-1-yl-propoxy)-phenyl]-imidazo[1,2-a]pyridine

HRID 1072034Notes

Reaction equation

HRID 1072034 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]3[CH:21]=2)=[C:8]([CH3:22])[CH:7]=1.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>>[N:23]1([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:13]=[C:14]4[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]4[CH:21]=3)=[C:8]([CH3:22])[CH:7]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

3

Reactant 2

HCID 8082PiperidineHCID 220156392-(4'-Chloropropoxy-2'-methylphenyl)-7-methylimidazo[1,2-a]pyridine

Product 1

HCID 102700937-Methyl-2-[2-methyl-4-(3-piperidin-1-yl-propoxy)-phenyl]-imidazo[1,2-a]pyridine

Procedure

The product of Step C (200 mg) and piperidine (2.0 mL) were heated at 100° C. for 2.5 hours. The reaction was cooled to ambient temperature and partitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL). The aqueous portion was extracted with additional ethyl acetate (10 mL) and the organic portions combined, washed with brine, and evaporated. The residue was purified via silica gel chromatography (dichloromethane/methanol) to give the title compound (110 mg). 1H-NMR (CD3OD) δ 8.28 (d, J=7.0 Hz, 1H), 7.78 (s, 1H), 7.61 (d, J=8.0 Hz, 1H), 7.31 (s, 1H), 6.84 (s, 1H), 6.79 (m, 2H), 4.04 (t, J=6.0 Hz, 2H), 2.50 (m, 12H), 1.99 (m, 2H), 1.64 (m, 4H), 1.51 (m, 2H)

Workup

  1. custompartitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL)
  2. extractionThe aqueous portion was extracted with additional ethyl acetate (10 mL)
  3. washwashed with brine
  4. customevaporated
  5. customThe residue was purified via silica gel chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-720826a324e542af90620dbf33563335
Source dataset
uspto-grants-2005_06
Patent number
US06908929B2

Reaction notes

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