1,4-Dioxane hydrochloride → Methyl 5-chloro-2-methyl-3-(piperidin-4-yloxy)benzoate, hydrochloride

HRID 1050467Notes

Reaction equation

HRID 1050467 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:23]([O:25][CH3:26])=[O:24])[C:5]([CH3:22])=[C:6]([CH:21]=1)[O:7][CH:8]1[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]1.Cl.O1CCOCC1>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:21]=[C:6]([O:7][CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[C:5]([CH3:22])=[C:4]([CH:3]=1)[C:23]([O:25][CH3:26])=[O:24]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 90273066Tert-butyl 4-(5-chloro-3-(methoxycarbonyl)-2-methylphenoxy)piperidine-1-carboxylate

Product 1

HCID 131736069Methyl 5-chloro-2-methyl-3-(piperidin-4-yloxy)benzoate, hydrochlorideYield 147.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-(5-chloro-3-(methoxycarbonyl)-2-methylphenoxy)piperidine-1-carboxylate (300 mg, 0.782 mmol) in DCM (3 mL) was treated with 4 M HCl/dioxane (3908 μl, 15.63 mmol) and stirred for 1 h at RT. The slurry was filtered and dried to give methyl 5-chloro-2-methyl-3-(piperidin-4-yloxy)benzoate, hydrochloride (0.185 g, 0.578 mmol, 74% yield). 1H NMR (400 MHz, DMSO-d6) δ 1.76-1.94 (m, 2 H) 2.02-2.16 (m, 2 H) 2.30 (s, 3 H) 2.99-3.13 (m, 2 H) 3.16-3.26 (m, 2 H) 3.83 (s, 3 H) 4.78 (dt, J=6.95, 3.60 Hz, 1 H) 7.34 (d, J=2.02 Hz, 1 H) 7.40 (d, J=2.02 Hz, 1 H) 8.83 (br. s., 2 H). MS(ES) [M+H]+ 284.1.

Workup

  1. filtrationThe slurry was filtered
  2. customdried

Sources & evidence

ORD record
ord-1ac69b4e2cfa4ac99895fdb756d963a8
Source dataset
uspto-grants-2016_07
Patent number
US09382234B2

Reaction notes

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