Hydrochloric Acid → Cyclohexanecarboxylic acid (2-chloro-4-hydroxy-benzyl)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amide, hydrochloride salt

HRID 1827538Notes

Reaction equation

HRID 1827538 reaction equation
[Cl:1][C:2]1[CH:31]=[C:30]([O:32]C2CCCCO2)[CH:29]=[CH:28][C:3]=1[CH2:4][N:5]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:16][CH:15]=1)[C:6]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].Cl.C(=O)(O)[O-].[Na+]>C(O)C>[ClH:1].[Cl:1][C:2]1[CH:31]=[C:30]([OH:32])[CH:29]=[CH:28][C:3]=1[CH2:4][N:5]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][CH2:26][CH2:27]2)=[CH:16][CH:15]=1)[C:6]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86760097Cyclohexanecarboxylic acid [2-chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-[4-(2-Pyrrolidin-1-yl-ethoxy)-phenyl]-amide

Product 1

HCID 131725781Cyclohexanecarboxylic acid (2-chloro-4-hydroxy-benzyl)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amide, hydrochloride saltYield 175.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of cyclohexanecarboxylic acid [2-chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amide (2.0 g) in 3:1 ethanol:1N HCl (40 mL) was stirred at room temperature for 1.5 hr. Saturated aqueous sodium bicarbonate solution was added and the aqueous solution was washed with methylene chloride. The organic solution was dried (magnesium sulfate), filtered and concentrated in vacuo. The crude product was purified by Biotage® chromatography (methylene chloride to 4% methanol/methylene chloride). The resulting white solid (1.53 g) was suspended in methanol (20 mL) and 4M HCl in dioxane was added. The mixture was stirred at room temperature for 1 hr. and was concentrated in vacuo to yield the title compound as a tan solid (1.60 g). MS 317.2 (MH+−40)

Workup

  1. washthe aqueous solution was washed with methylene chloride
  2. dry with materialThe organic solution was dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by Biotage® chromatography (methylene chloride to 4% methanol/methylene chloride)
  6. addition4M HCl in dioxane was added
  7. concentrationand was concentrated in vacuo

Sources & evidence

ORD record
ord-51a1fb68425b46f7aacb27e78f56cec4
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

Loading…