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Hydrochloric Acid → 4-Amino-piperidine-4-carboxylic acid 4-chloro-benzylamide dihydrochloride

HRID 2401564
Notes
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Reaction equation

HRID 2401564 reaction equation
[ClH:1].O1CCOCC1.C(OC([N:15]1[CH2:20][CH2:19][C:18]([NH:32]C(OC(C)(C)C)=O)([C:21](=[O:31])[NH: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][NH:22][C:21]([C:18]2([NH2:32])[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]2)=[O:31])=[CH:29][CH:28]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 451394444-Tert-butoxycarbonylamino-4-(4-chloro-benzylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 451396214-Amino-piperidine-4-carboxylic acid 4-chloro-benzylamide dihydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

A 4M solution of HCl in dioxane (7.7 ml, 31 mmol) was added dropwise to a solution of 4-tert-butoxycarbonylamino-4-(4-chloro-benzylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester (96 mg, 0.20 mmol) in methanol (7.7 mL) and stirred at rt for 17 h. The solvents were concentrated to give 4-amino-piperidine-4-carboxylic acid 4-chloro-benzylamide dihydrochloride (71 mg, 0.20 mmol, 100%) that was used in the next step without further purification.

Workup

  1. concentrationThe solvents were concentrated

Sources & evidence

ORD record
ord-97e9c8805e1f489fa4e00282fbe7ae90
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08796293B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes