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Hydrochloric Acid → 4-(4-Nitrophenyl)-1,2,3,6-tetrahydropyridine

HRID 2085411
Notes
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Reaction equation

HRID 2085411 reaction equation
CC(C)C(NC1C=CC=C(C2CCNCC2)C=1)=O.Cl.[N+:20]([C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH2:30][CH2:31][N:32](C(OC(C)(C)C)=O)[CH2:33][CH:34]=2)=[CH:25][CH:24]=1)([O-:22])=[O:21]>O1CCOCC1>[N+:20]([C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH:30]=2)=[CH:25][CH:24]=1)([O-:22])=[O:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 167572552-methyl-N-[3-(4-piperidyl)phenyl]propanamideHCID 22049016tert-butyl 5,6-dihydro-4-(4-nitrophenyl)pyridine-1(2H)-carboxylate

Product 1

HCID 220487834-(4-Nitrophenyl)-1,2,3,6-tetrahydropyridine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-(4-Nitrophenyl)-1,2,3,6-tetrahydropyridine was prepared by a similar procedure to that used for the preparation of 2-methyl-N-[3-(4-piperidinyl)phenyl]propanamide using HCl gas and tert-Butyl 4-(4-Nitrophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate (130 mg) in dioxane (5.0 mL) at room temperature. The reaction mixture was concentrated in vacuo to give the crude product (69.8 mg) that used in the next reaction without further purification.

Workup

  1. customat room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-53831d3c900142c2b258c9cff2735c9e
Source dataset
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06720324B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes