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Ammonium Chloride → 5-(Aminocarbonyl)-3-pyridyl 4-[2-(3-cyanophenyl)ethyl]-1-piperidinecarboxylate

HRID 605832
Notes
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Reaction equation

HRID 605832 reaction equation
Cl.C[N:3](C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[Cl-].[NH4+].[C:25]([C:27]1[CH:28]=[C:29]([CH2:33][CH2:34][CH:35]2[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]3[CH:45]=[N:46][CH:47]=[C:48]([CH:52]=3)[C:49](O)=[O:50])=[O:42])[CH2:37][CH2:36]2)[CH:30]=[CH:31][CH:32]=1)#[N:26].C(=O)([O-])O.[Na+]>CN(C=O)C>[C:25]([C:27]1[CH:28]=[C:29]([CH2:33][CH2:34][CH:35]2[CH2:36][CH2:37][N:38]([C:41]([O:43][C:44]3[CH:45]=[N:46][CH:47]=[C:48]([C:49]([NH2:3])=[O:50])[CH:52]=3)=[O:42])[CH2:39][CH2:40]2)[CH:30]=[CH:31][CH:32]=1)#[N:26]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 575078155-[({4-[2-(3-Cyanophenyl)ethyl]-1-piperidyl}carbonyl)oxy]nicotinic acid

Product 1

HCID 15950911
5-(Aminocarbonyl)-3-pyridyl 4-[2-(3-cyanophenyl)ethyl]-1-piperidinecarboxylate
Yield 79.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (62 mg), 1-hydroxybenzotriazole (43 mg), ammonium chloride (43 mg) and TEA (0.038 ml) were added to a DMF (3.0 ml) solution of 5-[({4-[2-(3-cyanophenyl)ethyl]-1-piperidyl}carbonyl)oxy]nicotinic acid (102 mg), followed by stirring overnight at room temperature. An aqueous saturated sodium hydrogencarbonate solution was added to the reaction liquid, and the crystal precipitated was collected by filtration and dried. The resulting crystal was recrystallized from EtOAc/hexane to give 5-(aminocarbonyl)-3-pyridyl 4-[2-(3-cyanophenyl)ethyl]-1-piperidinecarboxylate (81 mg).

Workup

  1. customthe crystal precipitated
  2. filtrationwas collected by filtration
  3. customdried
  4. customThe resulting crystal was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-f681a23c6a714d09b9f577d611c9ce19
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07915261B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes