Dichloromethane → 2-(2-Hydroxy-5-((piperidin-1-yl)methyl)benzamido)-4-phenylbenzoic acid hydrochloride

HRID 454646Notes

Reaction equation

HRID 454646 reaction equation
FC(F)(F)C(O)=O.COC[O:11][C:12]1[CH:39]=[CH:38][C:37]([CH2:40][N:41]2[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]2)=[CH:36][C:13]=1[C:14]([NH:16][C:17]1[CH:29]=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:27]=[CH:26][C:18]=1[C:19]([O:21]C(C)(C)C)=[O:20])=[O:15].C(Cl)[Cl:48]>>[ClH:48].[OH:11][C:12]1[CH:39]=[CH:38][C:37]([CH2:40][N:41]2[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]2)=[CH:36][C:13]=1[C:14]([NH:16][C:17]1[CH:29]=[C:28]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:27]=[CH:26][C:18]=1[C:19]([OH:21])=[O:20])=[O:15]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 66990064Tert-butyl 2-(2-(methoxymethoxy)-5-((piperidin-1-yl)methyl)benzamido)-4-phenylbenzoate

Product 1

HCID 669901172-(2-Hydroxy-5-((piperidin-1-yl)methyl)benzamido)-4-phenylbenzoic acid hydrochloride

Procedure

Under ice-cooling, trifluoroacetic acid (1.0 mL) was added to a methylene chloride (2.0 mL) solution of the obtained tert-butyl 2-(2-(methoxymethoxy)-5-((piperidin-1-yl)methyl)benzamido)-4-phenylbenzoate (0.080 g), followed by stirring at room temperature for 3 hours. The solvent was evaporated under reduced pressure, and ethyl acetate was added to the obtained residue. The solid substance was collected by filtration. Ethyl acetate (1.0 mL) and a 4.0 mol/L hydrogen chloride-dioxane solution (0.20 mL) were added to the obtained solid substance, followed by stirring at room temperature for 3 hours. The solid substance was collected from the reaction mixture by filtration to obtain 0.020 g of 2-(2-hydroxy-5-((piperidin-1-yl)methyl)benzamido)-4-phenylbenzoic acid hydrochloride as a white solid.

Workup

  1. temperatureUnder ice-cooling
  2. customThe solvent was evaporated under reduced pressure, and ethyl acetate
  3. additionwas added to the obtained residue
  4. filtrationThe solid substance was collected by filtration
  5. additionEthyl acetate (1.0 mL) and a 4.0 mol/L hydrogen chloride-dioxane solution (0.20 mL) were added to the obtained solid substance
  6. stirringby stirring at room temperature for 3 hours
  7. filtrationThe solid substance was collected from the reaction mixture by filtration

Sources & evidence

ORD record
ord-74abfd2fa74f4826a0d23c02ce206298
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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