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

HRID 1816773Notes

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

Participants

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

temperatureAfter cooling
filtrationthe reaction mixture was filtered
customevaporated
additionSodium hydrogen carbonate solution was added to the residue
filtrationAnd the resulting precipitate was collected by filtration
washwashed with water
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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