1,4'-Bipiperidine → 1,3-Dimethyl-7-[4-[6-(4-piperidinopiperidino)-nicotinoyl]benzyl]xanthine

HRID 1291419Notes

Reaction equation

HRID 1291419 reaction equation
Cl[C:2]1[CH:29]=[CH:28][C:5]([C:6]([C:8]2[CH:27]=[CH:26][C:11]([CH2:12][N:13]3[C:21]4[C:20](=[O:22])[N:19]([CH3:23])[C:18](=[O:24])[N:17]([CH3:25])[C:16]=4[N:15]=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][N:3]=1.[N:30]1([CH:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>N1C=CC=CC=1.O>[CH3:23][N:19]1[C:20](=[O:22])[C:21]2[N:13]([CH2:12][C:11]3[CH:26]=[CH:27][C:8]([C:6](=[O:7])[C:5]4[CH:28]=[CH:29][C:2]([N:39]5[CH2:40][CH2:41][CH:36]([N:30]6[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]6)[CH2:37][CH2:38]5)=[N:3][CH:4]=4)=[CH:9][CH:10]=3)[CH:14]=[N:15][C:16]=2[N:17]([CH3:25])[C:18]1=[O:24]

Participants

5

Reactant 2

HCID 786071,4'-BipiperidineHCID 189188457-[4-(6-Chloronicotinoyl)benzyl]-1,3-dimethylxanthine

Product 1

HCID 189190251,3-Dimethyl-7-[4-[6-(4-piperidinopiperidino)-nicotinoyl]benzyl]xanthineYield 41.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of 7-[4-(6-chloronicotinoyl)benzyl]-1,3-dimethylxanthine (196 mg) and 4-piperidinopiperidine (102 mg) in pyridine (10 ml) was stirred at 60° C. for 5 hours. This reaction mixture was poured in water and extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate: acetone: triethylamine 1:1:0.1) to provide the title compound (108 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate: acetone: triethylamine 1:1:0.1)

Sources & evidence

ORD record
ord-86f3f315b9044a4db53fbcd9e1a2322b
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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