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

HRID 2087145
Notes
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Reaction equation

HRID 2087145 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) which 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-5630d0787e4d4159b9802094f0b586c5
Source dataset
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06727264B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes