Piperidine → 2-(4-Piperidinopropoxyphenyl)-7-methylimidazo[1,2-a]pyridine

HRID 8355Notes

Reaction equation

HRID 8355 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)=[CH:8][CH:7]=1.[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>>[N:22]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)=[CH:8][CH:7]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 8082PiperidineHCID 142014602-(4-Chloropropoxyphenyl)-7-methylimidazo[1,2-a]pyridine

Product 1

HCID 102914892-(4-Piperidinopropoxyphenyl)-7-methylimidazo[1,2-a]pyridine

Procedure

The product of Step C (0.2 g) and piperidine (2.0 mL) were heated at reflux temperature for 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. The organic portions were dried over magnesium sulfate, filtered and evaporated. The residue was purified via silica gel chromatography (dichloromethane/methanol) to give the title compound (0.21 g). This compound can also be named as 7-(methyl-2-[4-(3-piperidin-1-yl-propoxy)-phenyl]-imidazo[1,2-a]pyridine. Treatment with 2M HCl in ether afforded the dihydrochloride. 1H NMR (CD3OD) δ 8.67 (d, J=7.5 Hz, 1H), 8.41 (s, 1H), 7.84 (m, 2H), 7.71 (s, 1H), 7.36 (dd, J=6.9 Hz, J=1.4 Hz, 1H), 7.16 (m, 2H), 4.22 (t, J=5.8 Hz, 2H), 3.64 (d, J=12.5 Hz, 2H), 3.35 (m, 2H), 3.04 (m, 2H), 2.62 (s, 3H), 2.34 (m, 2H), 1.99 (m, 2H), 1.86 (m, 3H), 1.59 (m, 1H); 13C NMR (CD3OD) δ 161.0, 147.1, 141.1, 136.2, 128.5, 128.2, 120.3, 119.3, 115.8, 110.6, 109.9, 65.8, 55.0, 53.8, 24.5, 23.6, 22.1, 21.2, MS (M+H)=350.2 Analysis: Calc'd for C22H27N3O 2HCl (2H2O) C, 57.64; H, 7.26; N, 9.17; Found: C, 57.68; H, 7.13; N, 9.16.

Workup

  1. temperatureat reflux temperature for 5 hours
  2. custompartitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL)
  3. extractionThe aqueous portion was extracted with additional ethyl acetate (10 mL)
  4. dry with materialThe organic portions were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified via silica gel chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-eccea7879e364388a1e2ea38cb936705
Source dataset
uspto-grants-2006_08
Patent number
US07087757B2

Reaction notes

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