Hydrochloric Acid → 2-Chloro-5-(4-piperidinylidenemethyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide, hydrochloride salt

HRID 2298082Notes

Reaction equation

HRID 2298082 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)=[CH:4][C:3]=1[C:22]([NH:24][CH2:25][C:26]12[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[CH2:27]1)[CH2:33]2)=[O:23].Cl>CO.O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)=[CH:4][C:3]=1[C:22]([NH:24][CH2:25][C:26]12[CH2:27][CH:28]3[CH2:29][CH:30]([CH2:31][CH:32]([CH2:34]3)[CH2:33]1)[CH2:35]2)=[O:23]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 867586494-[[4-Chloro-3-[[(tricyclo[3.3.1.13,7]dec-1-ylmethyl)amino]carbonyl]phenyl]methylene]-1-piperidinecarboxylic acid, 1,1-dimethylethyl ester

Product 1

HCID 1317236882-Chloro-5-(4-piperidinylidenemethyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide, hydrochloride saltYield 162.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-[[4-chloro-3-[[(tricyclo[3.3.1.13,7]dec-1-ylmethyl)amino]carbonyl]phenyl]methylene]-1-piperidinecarboxylic acid, 1,1-dimethylethyl ester (0.10 g, Example 50b) in methanol (3 ml) was treated with a 4N solution of hydrochloric acid in dioxane (1 ml) and stirred for 14 h at room temperature. The reaction mixture was concentrated under vacuum and the residue recrystallised from iso-propanol/ether to give the title compound as a white solid (0.071 g).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue recrystallised from iso-propanol/ether

Sources & evidence

ORD record
ord-ca6b70be831444f7ab7ae8359f81feb9
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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