Hydrochloric Acid → HCID 45139442, compound

HRID 2401577Notes

Reaction equation

HRID 2401577 reaction equation
[ClH:1].O1CCOCC1.C(OC([N:15]1[CH2:20][CH2:19][C:18]([NH:32]C(OC(C)(C)C)=O)([CH2:21][NH:22][C:23](=[O:31])[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].[NH2:32][C:18]1([CH2:21][NH:22][C:23](=[O:31])[C:24]2[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=2)[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66873110HCID 66873110, compound

Product 1

HCID 45139442HCID 45139442, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 4M solution of HCl in dioxane (0.3 ml, 1.2 mmol) was added dropwise to a solution of 4-tert-butoxycarbonylamino-4-[(4-chloro-benzoylamino)-methyl]-piperidine-1-carboxylic acid tert-butyl ester (5.8 mg, 0.012 mmol) in methanol (0.5 mL). The solution was stirred at room temperature for 17 hours. The solvents were concentrated to give N-(4-amino-piperidin-4-ylmethyl)-4-chloro-benzamide dihydrochloride (6.1 mg, quantitative) that was used in the next step without further purification. 1H NMR (CD3OD) δ 2.23-2.30 (4H, m), 3.46-3.61 (4H, m), 3.89 (2H, s), 7.58 (2H, d, J=7 Hz), 8.03 (2H, d, J=7 Hz).

Workup

  1. concentrationThe solvents were concentrated

Sources & evidence

ORD record
ord-dacb8999535e443394db996578c67dfe
Source dataset
uspto-grants-2014_08
Patent number
US08796293B2

Reaction notes

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