Hydrochloric Acid → Piperidine, 4-[4-(4-chlorophenoxy)phenoxy]-, hydrochloride (1:1)

HRID 2103323Notes

Reaction equation

HRID 2103323 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:19]=[CH:18][C:10]([O:11][CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.Cl>O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:19]=[CH:18][C:10]([O:11][CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 24883361HCID 24883361, compound

Product 1

HCID 69004120Piperidine, 4-[4-(4-chlorophenoxy)phenoxy]-, hydrochloride (1:1)Yield 92.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the product from step 1 (0.88 g, 2.17 mmol) was added 4 M HCl in dioxane (10 mL). The resulting mixture was stirred at ambient temperature for 2 hours. The solvent was removed under reduced pressure. The residue was triturated with ether to afford the title compound (0.34 g, 47%) as a white solid; 1H NMR (400 MHz, DMSO-d6); δ 1.83 (m, 2H), 2.09 (m, 2H), 3.06 (m, 2H), 3.23 (m, 2H), 4.60 (m, 1H), 6.94 (d, J=9.2 Hz, 2H), 7.01-7.06 (m, 4H), 7.40 (d, J=9.2 Hz, 2H), 8.81 (br s, 2H); MS (m/z) 304.4 (M+1); LC (100%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-860e5fc2024f4f11a183a5fdf939c8a1
Source dataset
uspto-grants-2009_08
Patent number
US07576102B2

Reaction notes

Loading…