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

HRID 1520033
Notes
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Reaction equation

HRID 1520033 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:12][CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15][CH:16]=2)=[CH:7][CH:6]=1)([O-:4])=[O:3]>O1CCOCC1.C1(C)C=CC=CC=1>[ClH:1].[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH:12]=2)=[CH:7][CH:6]=1)([O-:4])=[O:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22049016tert-butyl 5,6-dihydro-4-(4-nitrophenyl)pyridine-1(2H)-carboxylate

Product 1

HCID 679842994-(4-Nitrophenyl)-1,2,3,6-tetrahydropyridine hydrochlorideYield 97%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

Hydrogen chloride (20 mL of a 4N solution in dioxane) was added dropwise to a solution of tert-butyl 4-(4-nitrophenyl)-3,6-dihydropyridine-1(2H)-carboxylate (3.0 g; 9.86 mmol; 1.0 eq.) in toluene (15 mL). The reaction mixture was stirred at RT for 3 h. The formed suspension was filtered, washed with toluene (10 mL) and dried under vacuum to give the title compound as a white solid (1.96 g, 97%). UPLC/MS: (MS+) 205.3.

Workup

  1. filtrationThe formed suspension was filtered
  2. washwashed with toluene (10 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-c5cd66c1b5f24861a0e5cc9408c06220
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09073892B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes