Piperidine → HCID 22015611, compound

HRID 1268682

Reaction equation

HRID 1268682 reaction equation
Br.Cl[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]3[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][N:16]3[CH:22]=2)=[CH:9][C:8]=1[O:23][CH3:24].[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>>[N:25]1([CH2:3][CH2:4][CH2:5][O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:14]=[C:15]4[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][N:16]4[CH:22]=3)=[CH:9][C:8]=2[O:23][CH3:24])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

3

Reactant 2

HCID 8082PiperidineHCID 220155982-(4'-Chloropropoxy-3'-methoxyphenyl)-7-methylimidazo[1,2-a]pyridine hydrobromide

Product 1

HCID 22015611HCID 22015611, compound

Procedure

The product of Step C (184 mg) and piperidine (1.5 mL) were heated at 100° C. for 4 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 twice with additional ethyl acetate (10 mL) and once with dichloromethane (10 mL). The organic portions were combined, washed with brine, and evaporated. The residue was purified via silica gel chromatography (dichloromethane/2M ammonia in methanol) to give the title compound (150 mg). 1H-NMR (CD3OD) δ8.17 (d, J=7.0 Hz, 1H), 7.93 (s, 1H), 7.50 (d, J=2.0 Hz, 1H), 7.38 (dd, J=8.0 Hz, J=2.0 Hz, 1H), 7.26 (s, 1H), 6.93 (d, J=8.0 Hz, 1H), 6.68 (dd, J=7.0 Hz, J=1.5 Hz, 1H), 4.00 (t, J=6.0 Hz, 2H), 3.91 (s, 3H), 2.56 (m, 3H), 2.48 (br. s, 3H), 2.38 (s, 3H), 1.98 (m, 2H), 1.60 (m, 4H), 1.47 (m, 2H)

Workup

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

Sources & evidence

ORD record
ord-1af8865c171344c0b058c041095b41b6
Source dataset
uspto-grants-2007_04
Patent number
US07199117B2

Linked notes

Loading…