Hydrochloric Acid → Morpholine-4-carboxylic acid [1-(4-cyano-piperidin-4-ylcarbamoyl)-2-cyclohexyl-ethyl]-amide hydrochloride

HRID 353933Notes

Reaction equation

HRID 353933 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:34]#[N:35])([NH:14][C:15](=[O:33])[CH:16]([NH:24][C:25]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[O:26])[CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:36]>O1CCOCC1>[ClH:36].[C:34]([C:11]1([NH:14][C:15]([CH:16]([NH:24][C:25]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[O:26])[CH2:17][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)=[O:33])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)#[N:35]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 694173464-Cyano-4-{3-cyclohexyl-2-[(morpholine-4-carbonyl)-amino]-propionylamino}-piperidine-1-carboxylic acid t-butyl ester

Product 1

HCID 22260409Morpholine-4-carboxylic acid [1-(4-cyano-piperidin-4-ylcarbamoyl)-2-cyclohexyl-ethyl]-amide hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-Cyano-4-{3-cyclohexyl-2-[(morpholine-4-carbonyl)-amino]-propionylamino}-piperidine-1-carboxylic acid t-butyl ester (1000 mg, 2.03 mmol) was dissolved in 20 mL of 4 M HCl in dioxane and stirred for 1 hour at which time the volatiles were remove in vacuo. The resulting residue was triturated with 100 mL of diethyl ether and the resulting solid was collected by filtration under inert atmosphere (the solid is very hygroscopic) and washed 2×50 mL of diethyl ether and dried in vacuo to yield the title compound as a bright white powder (802 mg); MS, m/z 392, M-35).

Workup

  1. customwere remove in vacuo
  2. customThe resulting residue was triturated with 100 mL of diethyl ether
  3. filtrationthe resulting solid was collected by filtration under inert atmosphere (the solid
  4. washwashed 2×50 mL of diethyl ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-c944967ae682439ba0f5ab2eb5f8c757
Source dataset
uspto-grants-2004_06
Patent number
US06756372B2

Reaction notes

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