Triethylamine → 4-Benzyloxycarbonyl-1-{[4-ethoxycarbonylamino-1-(2-methyl-4-pyridyl)-4-piperidiny]methyl}-2-piperazinone

HRID 2214814Notes

Reaction equation

HRID 2214814 reaction equation
Cl.Cl[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH3:9])[CH:4]=1.C(N(CC)CC)C.[CH2:17]([O:24][C:25]([N:27]1[CH2:32][CH2:31][N:30]([CH2:33][C:34]2([NH:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[C:29](=[O:46])[CH2:28]1)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[CH2:17]([O:24][C:25]([N:27]1[CH2:32][CH2:31][N:30]([CH2:33][C:34]2([NH:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:35][CH2:36][N:37]([C:3]3[CH:8]=[CH:7][N:6]=[C:5]([CH3:9])[CH:4]=3)[CH2:38][CH2:39]2)[C:29](=[O:46])[CH2:28]1)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27628414-chloro-2-methylpyridine hydrochlorideHCID 219482974-Benzyloxycarbonyl-1-[(4-ethoxycarbonylamino-4-piperidinyl)methyl]-2-piperazinone

Product 1

HCID 219483344-Benzyloxycarbonyl-1-{[4-ethoxycarbonylamino-1-(2-methyl-4-pyridyl)-4-piperidiny]methyl}-2-piperazinoneYield 53.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Chloro-2-methylpyridine hydrochloride (941 mg), triethylamine (1.93 g) and ethanol (50 ml) were added to 4-benzyloxycarbonyl-1-[(4-ethoxycarbonylamino-4-piperidinyl)methyl]-2-piperazinone (2.0 g), and the mixture was reacted at 150° C. for 10 hours in a sealed tube. The reaction mixture was concentrated, a 10% aqueous sodium carbonate solution was added to the residue, and the mixture was extracted with dichloromethane, dried, and concentrated. The resulting residue was purified by column chromatography (dichloromethane:10% aqueous ammonia-containing methanol=20:1) to obtain the colorless amorphous title compound (1.31 g).

Workup

  1. customthe mixture was reacted at 150° C. for 10 hours in a sealed tube
  2. concentrationThe reaction mixture was concentrated
  3. additiona 10% aqueous sodium carbonate solution was added to the residue
  4. extractionthe mixture was extracted with dichloromethane
  5. customdried
  6. concentrationconcentrated
  7. customThe resulting residue was purified by column chromatography (dichloromethane:10% aqueous ammonia-containing methanol=20:1)

Sources & evidence

ORD record
ord-d5bbfc57c57343f5b73ceab29749b51f
Source dataset
uspto-grants-2006_09
Patent number
US07109200B2

Reaction notes

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