Triethylamine → HCID 86653000, compound

HRID 1850834Notes

Reaction equation

HRID 1850834 reaction equation
[Cl-].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH:13]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH2:24][CH2:25][NH:26][S:27]([CH2:30][CH2:31][CH3:32])(=[O:29])=[O:28])[CH:21]=4)[CH2:16][CH2:15][NH2+:14]3)[CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[H][H]>CO.[Pd]>[Cl-:2].[C:6]1([C:9]2([CH:13]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH2:24][CH2:25][NH:26][S:27]([CH2:30][CH2:31][CH3:32])(=[O:29])=[O:28])[CH:21]=4)[CH2:16][CH2:15][NH2+:14]3)[CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:4][CH:3]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 87184342HCID 87184342, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86653000HCID 86653000, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-(1-(4-Chlorophenyl)cyclobutyl)-7-(2-(propylsulfonamido)ethoxy)-1,2,3,4-tetrahydroisoquinolinium chloride (187 mg, 0.374 mmol, example 4), triethylamine (91 mg, 0.897 mmol), Pd/C (11.95 mg, 0.011 mmol) were suspended in dry MeOH (5 ml) and treated with hydrogen gas at ambient pressure for 14 h. The solvent was removed and the residue was purified by column chromatography using silica gel dichloromethane/methanol (97:3→95:5) as the eluent. The product was transferred into the hydrochloride with isopropylether and HCl dissolved in isopropanol (6%). The product was obtained as a white powder (68.0 mg, 0.146 mmol, 39%.)

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by column chromatography
  3. dissolutiondissolved in isopropanol (6%)
  4. customThe product was obtained as a white powder (68.0 mg, 0.146 mmol, 39%.)

Sources & evidence

ORD record
ord-8d50cc3848f04a1fa65fb6b04aea4bb0
Source dataset
uspto-grants-2015_02
Patent number
US08957089B2

Reaction notes

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