Ammonium formate → 1-[1-(4-Pyrimidinyl)-4-piperidylcarbonyl]piperazine

HRID 2289524Notes

Reaction equation

HRID 2289524 reaction equation
C([O-])=O.[NH4+].C([N:12]1[CH2:17][CH2:16][N:15]([C:18]([CH:20]2[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][N:29]=[CH:28][N:27]=3)[CH2:22][CH2:21]2)=[O:19])[CH2:14][CH2:13]1)C1C=CC=CC=1>[Pd].CO>[N:29]1[CH:30]=[CH:31][C:26]([N:23]2[CH2:22][CH2:21][CH:20]([C:18]([N:15]3[CH2:14][CH2:13][NH:12][CH2:17][CH2:16]3)=[O:19])[CH2:25][CH2:24]2)=[N:27][CH:28]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 186980661-Benzyl-4-[(1-[4-pyrimidinyl]-4-piperidyl)carbonyl]piperazine

Product 1

HCID 186979701-[1-(4-Pyrimidinyl)-4-piperidylcarbonyl]piperazineYield 94.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ammonium formate (1.88 g) was added to a mixture of 1-benzyl-4-[1-(4-pyrimidinyl) -4-piperidylcarbonyl]piperazine (2.73 g) and 10% palladium on carbon catalyst (0.55 g) in methanol (70 ml) under an atmosphere of argon. The mixture was stirred under reflux for 1 hour. The cooled mixture was filtered through diatomaceous earth and the filtercake was well washed with methanol. The filtrate and washings were combined and evaporated. The residual oil was suspended in saturated aqueous sodium carbonate solution (30 ml) and the mixture was extracted with dichloromethane (4×100 ml). The dichloromethane extracts were combined, dried (Na2SO4) and evaporated to give 1-[1-(4-pyrimidinyl)-4-piperidylcarbonyl]piperazine (1.94 g, 94%) as an off-white solid; NMR (CDCl3): 1.75-1.95 (m, 4H), 2.7-3.15 (m, 8H), 3.4-3.7 (m, 4H), 4.3-4.47 (m, 2H), 6.45-6.55 (d, 1H), 8.12-8.23 (d, 1H) and 8.52-8.63 (s, 1H); m/z 276 (M+H).

Workup

  1. temperatureunder reflux for 1 hour
  2. filtrationThe cooled mixture was filtered through diatomaceous earth
  3. washthe filtercake was well washed with methanol
  4. customevaporated
  5. extractionthe mixture was extracted with dichloromethane (4×100 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-ebe6964d84eb4511aec857012e646b58
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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