Hydrochloric Acid → N-(2-Aminophenyl)-4-piperidin-4-ylbenzamide

HRID 888008

Reaction equation

HRID 888008 reaction equation
Cl.C(OC([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17](=[O:37])[C:18]1[CH:23]=[CH:22][C:21]([CH:24]2[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]2)=[CH:20][CH:19]=1)=O)(C)(C)C>O1CCOCC1>[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17](=[O:37])[C:18]1[CH:23]=[CH:22][C:21]([CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68407604N-(2-t-butoxycarbonylaminophenyl)-4-(1-t-butoxycarbonylpiperidin-4-yl)benzamide

Product 1

HCID 16225584N-(2-Aminophenyl)-4-piperidin-4-ylbenzamideYield 82%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A 4M solution of hydrogen chloride in dioxane (5 ml, 20 mmol) was added to a stirred solution of N-(2-t-butoxycarbonylaminophenyl)-4-(1-t-butoxycarbonylpiperidin-4-yl)benzamide (Method 15, 693 mg, 1.40 mmol) in 1,4-dioxane (5 ml) and the mixture stirred at ambient temperature for 18 hours. The resultant precipitate was filtered and washed with diethyl ether. The resultant solid was dissolved in water and basified to pH 12 with 2M solution of aqueous sodium hydroxide. The resultant precipitate was filtered, washed with water and dried in vacuo to give the title compound (338 mg, 82%); NMR Spectrum: (DMSO-d6) 1.52 (m, 2H), 1.69 (m, 2H), 2.60 (m, 3H), 3.02 (m, 2H), 4.84 (br, 2H), 6.58 (m, 1H), 6.76 (d, 1H), 6.95 (m, 1H), 7.16 (d, 1H), 7.34 (d, 2H), 7.89 (d, 2H), 9.53 (br, 1H); Mass Spectrum: M+H+ 296.

Workup

  1. filtrationThe resultant precipitate was filtered
  2. washwashed with diethyl ether
  3. dissolutionThe resultant solid was dissolved in water and basified to pH 12 with 2M solution of aqueous sodium hydroxide
  4. filtrationThe resultant precipitate was filtered
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-cdb7e8ef782046b68c8b4e2280a0456b
Source dataset
uspto-grants-2012_08
Patent number
US08247562B2

Linked notes

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