Hydrochloric Acid → 4-(7-Fluoro-2,3-dihydrobenzofuran-2-yl)piperidine hydrochloride

HRID 1025497Notes

Reaction equation

HRID 1025497 reaction equation
[F:1][C:2]1[C:10]2[O:9][CH:8]([CH:11]3[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]3)[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[ClH:24].O1CCOCC1>CO>[ClH:24].[F:1][C:2]1[C:10]2[O:9][CH:8]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67467702tert-Butyl 4-(7-fluoro-2,3-dihydrobenzofuran-2-yl)piperidine-1-carboxylate

Product 1

HCID 674657554-(7-Fluoro-2,3-dihydrobenzofuran-2-yl)piperidine hydrochlorideYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-(7-fluoro-2,3-dihydrobenzofuran-2-yl)piperidine-1-carboxylate (2.36 g, 7.34 mmol) in MeOH (43.2 mL) was added HCl in dioxane (4 M, 26.8 mL, 107 mmol). Upon completion of addition, the mixture was stirred at room temperature for 5 h. After this time, the solvent was removed under reduced pressure to afford Compound 3D as a yellow oil (1.826 g, 97% yield), which was used in the next reaction without further purification. LC/MS (m/z)=222 (M+H)+.

Workup

  1. additionUpon completion of addition
  2. customAfter this time, the solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-009adf7e38ee4606af95d4af73edecbc
Source dataset
uspto-grants-2014_05
Patent number
US08729084B2

Reaction notes

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