Hydrochloric Acid → HCID 10171718, compound

HRID 888015Notes

Reaction equation

HRID 888015 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:29])[C:17]1[CH:22]=[CH:21][C:20]([CH:23]2[CH2:28][CH2:27][CH2:26][NH:25][CH2:24]2)=[CH:19][CH:18]=1)=O)(C)(C)C.Cl>O1CCOCC1>[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:29])[C:17]1[CH:22]=[CH:21][C:20]([CH:23]2[CH2:28][CH2:27][CH2:26][NH:25][CH2:24]2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68406528HCID 68406528, compound

Product 1

HCID 10171718HCID 10171718, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (RS)—N-(2-t-butoxycarbonylaminophenyl)-4-piperidin-3-ylbenzamide (1.0 g, 2.5 mmol) in 1,4-dioxane (9.5 ml) was added a solution of hydrogen chloride (4M in 1,4-dioxane, 9.5 ml, 38 mmol) and the mixture stirred at ambient temperature for 6 hours. The solid formed was collected by filtration, washed with diethyl ether and dried in vacuo. It was treated with a 2M solution of aqueous sodium hydroxide and extracted three times with ethyl acetate. The combined organic extracts were dried over magnesium sulfate and evaporated to afford the product as a colourless solid (0.73 g, 99%); NMR Spectrum: (DMSO-d6) 1.71 (m, 4H), 2.61 (m, 2H), 2.75 (m, 1H), 3.03 (m, 2H), 4.92 (s, 2H), 6.65 (t, 1H), 6.83 (d, 1H), 7.02 (t, 1H), 7.23 (d, 1H), 7.42 (d, 2H), 7.96 (d, 2H), 9.61 (s, 1H); Mass Spectrum: M+H+ 296.

Workup

  1. customThe solid formed
  2. filtrationwas collected by filtration
  3. washwashed with diethyl ether
  4. customdried in vacuo
  5. additionIt was treated with a 2M solution of aqueous sodium hydroxide
  6. extractionextracted three times with ethyl acetate
  7. dry with materialThe combined organic extracts were dried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-900b023f49e043a8b5285cd4589b09d8
Source dataset
uspto-grants-2012_08
Patent number
US08247562B2

Reaction notes

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