Hydrochloric Acid → 4-(4-Chloro-benzyloxymethyl)-piperidin-4-ylamine dihydrochloride

HRID 2406007Notes

Reaction equation

HRID 2406007 reaction equation
[ClH:1].O1CCOCC1.C(OC([N:15]1[CH2:20][CH2:19][C:18]([NH:31]C(OC(C)(C)C)=O)([CH2:21][O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>CO>[ClH:30].[ClH:1].[Cl:30][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][O:22][CH2:21][C:18]2([NH2:31])[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 668728604-Tert-butoxycarbonylamino-4-(4-chloro-benzyloxymethyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 451394394-(4-Chloro-benzyloxymethyl)-piperidin-4-ylamine dihydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 4M solution of HCl in dioxane (0.68 ml, 2.7 mmol) was added dropwise to a solution of 4-tert-butoxycarbonylamino-4-(4-chloro-benzyloxymethyl)-piperidine-1-carboxylic acid tert-butyl ester (12 mg, 0.028 mmol) in methanol (1 mL). The solution was stirred at rt for 17 h. The solvents were removed by evaporation to give 4-(4-chloro-benzyloxymethyl)-piperidin-4-ylamine dihydrochloride (9.2 mg, 0.028 mmol, 100%) that was used in the next step without further purification. 1H NMR (500 MHz, CD3OD): 2.12-2.24 (4H, m), 3.22-3.32 (2H, m), 3.42-3.45 (2H, m), 3.75 (2H, s), 4.66 (2H, s), 7.38-7.43 (4H, m).

Workup

  1. customThe solvents were removed by evaporation

Sources & evidence

ORD record
ord-16612c11d48d47399227bbb43e3a111d
Source dataset
uspto-grants-2014_08
Patent number
US08809336B2

Reaction notes

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