Hydrochloric Acid → N-{1-[(1-Aminocyclobutyl)carbonyl]-5-(3,4-dimethylphenyl)piperidin-3-yl}benzenecarboxamide hydrochloride

HRID 876318Notes

Reaction equation

HRID 876318 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:14][CH:13]([NH:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:17])[CH2:12][N:11]([C:24]([C:26]3([NH:30]C(=O)OC(C)(C)C)[CH2:29][CH2:28][CH2:27]3)=[O:25])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8].[ClH:38]>O1CCOCC1>[ClH:38].[NH2:30][C:26]1([C:24]([N:11]2[CH2:10][CH:9]([C:4]3[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=3)[CH2:14][CH:13]([NH:15][C:16]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:17])[CH2:12]2)=[O:25])[CH2:27][CH2:28][CH2:29]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68075430tert-Butyl [1-({3-(3,4-dimethylphenyl)-5-[(phenylcarbonyl)amino]piperidin-1-yl}carbonyl)cyclobutyl]carbamate

Product 1

HCID 66761349N-{1-[(1-Aminocyclobutyl)carbonyl]-5-(3,4-dimethylphenyl)piperidin-3-yl}benzenecarboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

55 mg (0.14 mmol) of tert-butyl [1-({3-(3,4-dimethylphenyl)-5-[(phenylcarbonyl)amino]piperidin-1-yl}carbonyl)cyclobutyl]carbamate were dissolved in 7 ml of dioxane, 1.5 ml of concentrated hydrochloric acid were added and the mixture was immediately concentrated on a rotary evaporator. The residue was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 19 mg (39% of theory)

Workup

  1. concentrationthe mixture was immediately concentrated on a rotary evaporator
  2. customThe residue was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient)

Sources & evidence

ORD record
ord-3a9b100e8a654224a42c731491c8b6af
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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