Hydrochloric Acid → (R)-2-(((4-amino-2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)methyl)piperidinium hydrochloride

HRID 332960Notes

Reaction equation

HRID 332960 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:14][O:15][C:16]1[C:25]2[C:24]([NH2:26])=[N:23][S:22](=[O:28])(=[O:27])[NH:21][C:20]=2[CH:19]=[CH:18][CH:17]=1)=O)(C)(C)C.[ClH:29]>C(O)C>[ClH:29].[NH2:26][C:24]1[C:25]2[C:16]([O:15][CH2:14][C@H:9]3[CH2:10][CH2:11][CH2:12][CH2:13][NH2+:8]3)=[CH:17][CH:18]=[CH:19][C:20]=2[NH:21][S:22](=[O:27])(=[O:28])[N:23]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86714284(R)-tert-butyl 2-(((4-amino-2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)methyl)piperidine-1-carboxylate

Product 1

HCID 86714283(R)-2-(((4-amino-2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)methyl)piperidinium hydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of (R)-tert-butyl-2-(((4-amino-2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)methyl)piperidine-1-carboxylate (Example 15b, 10.7 g, 26.1 mmol) in ethanol (175 mL) was added HCl in ethanol (104 mL, 2.5M, 261 mmol). The reaction stirred at 60° C. under nitrogen for 4 hours. The compound was collected by filtration as an off white solid (7.70 g, 85% yield for three steps). 1H NMR (400 MHz, DMSO-d6) δ 1.03-1.90 (br m, 6H), 2.89 (br t, J=2.8 Hz, 1H), 3.27 (br m, 1H), 3.61 (br m, 1H), 4.27-4.40 (br m, 2H), 6.67 (d, J=7.6 Hz, 1H), 6.80 (d, J=8.8 Hz, 1H), 7.46 (t, J=8.0 Hz, 1H), 7.79 (br s, 1H), 8.35 (br s, 1H), 9.26 (br s, 2H), 10.97 (br s, 1H). MS 311 (MH+).

Workup

  1. filtrationThe compound was collected by filtration as an off white solid (7.70 g, 85% yield for three steps)

Sources & evidence

ORD record
ord-790ebb03cb9747f19b910a1126ad0226
Source dataset
uspto-grants-2014_11
Patent number
US08877922B2

Reaction notes

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