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

HRID 270022Notes

Reaction equation

HRID 270022 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][N:11](C(OC(C)(C)C)=O)[CH2:12][CH:13]=2)=[CH:4][CH:3]=1.Cl>ClCCl.C(OCC)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 157514261,1-Dimethylethyl 4-(4-fluorophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate

Product 1

HCID 1977484-(4-Fluorophenyl)-1,2,3,6-tetrahydropyridineYield 141.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of Example 6B (0.5 g, 1.8 mmol) in dichloromethane (5 mL) at room temperature was treated with 2M HCl in diethyl ether (5 mL), stirred overnight, and concentrated to provide the desired product (0.45 g, 95%). MS (ESI) m/e 178 (M+H)+.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-20cade794db14fc7a19545c941ce0f51
Source dataset
uspto-grants-2008_11
Patent number
US07449485B2

Reaction notes

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