Hydrochloric Acid → HCID 67972354, compound

HRID 331402Notes

Reaction equation

HRID 331402 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:19]3[CH:20]=[CH:21][O:22][C:18]=3[C:17]([F:23])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:24]>ClCCl>[ClH:24].[F:23][C:17]1[C:18]2[O:22][CH:21]=[CH:20][C:19]=2[C:14]([C:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67972151HCID 67972151, compound

Product 1

HCID 67972354HCID 67972354, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(7-fluoro-benzofuran-4-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.97 g, 3.06 mmol) in dichloromethane (23 ml) was added at room temperature hydrochloric acid solution (4M in dioxane, 11.5 ml, 45.8 mmol) and the reaction mixture was allowed to stir for 1.5 h. The reaction mixture was evaporated, the residue triturated with diethyl ether (50 ml) and MeOH (1 ml), the precipitate was collected by filtration, washed with diethyl ether and dried to yield 4-(7-fluoro-benzofuran-4-yl)-1,2,3,6-tetrahydro-pyridine hydrochloride as light yellow solid (0.7 g, 90%), MS (ISP) m/z=218.2 [(M+H)+], mp 202° C.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue triturated with diethyl ether (50 ml) and MeOH (1 ml)
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-7a85168600c54b748b4af98cbd512ab5
Source dataset
uspto-grants-2014_11
Patent number
US08877778B2

Reaction notes

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