Hydrochloric Acid → 1-(3-Amino-benzyl)-piperidine-4-carboxylic acid cyclohexylamide

HRID 1486692Notes

Reaction equation

C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([C:21](=[O:29])[NH:22][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:17][CH2:16]2)[CH:9]=1)(C)(C)C.Cl.[OH-].[Na+]>O1CCOCC1>[CH:23]1([NH:22][C:21]([CH:18]2[CH2:17][CH2:16][N:15]([CH2:14][C:10]3[CH:11]=[CH:12][CH:13]=[C:8]([NH2:7])[CH:9]=3)[CH2:20][CH2:19]2)=[O:29])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of [3-(4-cyclohexylcarbamoyl-piperidin-1-ylmethyl)-phenyl]-carbamic acid tert-butyl ester (4.6 g, 11.1 mmol) in 1,4-dioxane (110 mL) is cooled down to 0° C. and treated with a 4N HCl solution in 1,4-dioxane (24.9 mL, 99.6 mmol). The reaction mixture is heated to 60° C. for 1 h. The reaction mixture is cooled down to RT and treated with aqueous 2N sodium hydroxide. After evaporation of 1,4-dioxane under reduced pressure the reaction mixture is extracted twice with DCM (110 mL). The combined organic phases are dried over MgSO4 and evaporated to yield the title compound as a yellowish powder: LC-MS A: tR=0.50 min; [M+H]+=316.32.

Workup

temperatureThe reaction mixture is cooled down to RT
customAfter evaporation of 1,4-dioxane under reduced pressure the reaction mixture
extractionis extracted twice with DCM (110 mL)
dry with materialThe combined organic phases are dried over MgSO4
customevaporated

Sources & evidence

ORD record: ord-0d48e3b40a5c450fad1747784f1ac016
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428456B2

Reaction notes

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