Piperidine → 2-[4-(3-Piperidin-1-yl-propoxy)-phenyl]-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine

HRID 8362

Reaction equation

HRID 8362 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[CH2:19][CH2:18][CH2:17][CH2:16][N:15]3[CH:20]=2)=[CH:8][CH:7]=1.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>>[N:21]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[CH2:19][CH2:18][CH2:17][CH2:16][N:15]4[CH:20]=3)=[CH:8][CH:7]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 8082PiperidineHCID 220156272-[4-(3-Chloro-propoxy)-phenyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

Product 1

HCID 98408562-[4-(3-Piperidin-1-yl-propoxy)-phenyl]-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine

Procedure

The product of Step B (83 mg) and piperidine (1.0 mL) were heated at 100° C. for 1.5 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 a fresh portion of ethyl acetate (2×10 mL) and the organic portions combined and washed with brine (10 mL). 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 (35 mg). 1H-NMR (CDCl3) δ 7.61 (m, 2H), 7.16 (s, 1H), 6.92 (m, 2H), 4.01 (m, 4H), 2.84 (t, J=6.0 Hz, 2H), 2.72 (m, 6H), 2.00 (m, 6H), 1.68 (m, 4H), 1.56 (m, 2H).

Workup

  1. custompartitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL)
  2. extractionThe aqueous portion was extracted with a fresh portion of ethyl acetate (2×10 mL)
  3. washwashed with brine (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-5cc812fae5524069a85a9f6a363f1a03
Source dataset
uspto-grants-2006_08
Patent number
US07087757B2

Linked notes

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