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Ammonium formate → 1-[4-[4-[4-(4-Methoxybutoxy)phenyl]piperidin-1-yl]phenyl]piperazine

HRID 1816773
Notes
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Reaction equation

HRID 1816773 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:28][CH:27]=[C:26]([C:29]4[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][O:40][CH3:41])=[CH:31][CH:30]=4)[CH2:25][CH2:24]3)=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.O1CCOCC1.[Pd]>[CH3:41][O:40][CH2:39][CH2:38][CH2:37][CH2:36][O:35][C:32]1[CH:33]=[CH:34][C:29]([CH:26]2[CH2:27][CH2:28][N:23]([C:20]3[CH:19]=[CH:18][C:17]([N:14]4[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]4)=[CH:22][CH:21]=3)[CH2:24][CH2:25]2)=[CH:30][CH:31]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 696777324-[4-[4-[4-(4-methoxybutoxy)phenyl]-3,6-dihydro-2H-pyridin-1-yl]phenyl]piperazine-1-carboxylic acid benzyl ester

Product 1

HCID 224946411-[4-[4-[4-(4-Methoxybutoxy)phenyl]piperidin-1-yl]phenyl]piperazineYield 81.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst
HCID 887
Methanol
Solvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 4-[4-[4-[4-(4-methoxybutoxy)phenyl]-3,6-dihydro-2H-pyridin-1-yl]phenyl]piperazine-1-carboxylic acid benzyl ester (2.20 g) and ammonium formate (1.25 g) in 90% methanol (44 ml) and dioxane was added 10% palladium on carbon at room temperature. The reaction mixture was heated at 100° C. for 2 hours. After cooling, the reaction mixture was filtered and evaporated. Sodium hydrogen carbonate solution was added to the residue. And the resulting precipitate was collected by filtration, washed with water and dried under hi-vacuum to give 1-[4-[4-[4-(4-methoxybutoxy)phenyl]piperidin-1-yl]phenyl]piperazine (1.36 g).

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. customevaporated
  4. additionSodium hydrogen carbonate solution was added to the residue
  5. filtrationAnd the resulting precipitate was collected by filtration
  6. washwashed with water
  7. customdried under hi-vacuum

Sources & evidence

ORD record
ord-fbf4101dc8404ba9aa56b03d817d6072
Source dataset
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06884868B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes