Acetic Acid → HCID 178464127, compound

HRID 2402596Notes

Reaction equation

HRID 2402596 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][C:19]=2[CH3:20])[C:16](=[O:21])[NH:15][CH:14]=[CH:13]3)[CH2:5][CH2:4]1.[C:22](O)(=O)[CH3:23].[CH:26](=O)[CH3:27].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(Cl)Cl>[CH2:26]([N:2]([CH2:22][CH3:23])[C@@H:3]1[CH2:4][CH2:5][C@H:6]([O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][C:19]=2[CH3:20])[C:16](=[O:21])[NH:15][CH:14]=[CH:13]3)[CH2:7][CH2:8]1)[CH3:27]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 178422250HCID 178422250, compound

Product 1

HCID 178464127HCID 178464127, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A reaction mixture consisting of 150 mg (0.49 mmol) 6-(cis-4-amino-cyclohexyloxy)-7-methyl-2H-isoquinolin-1-one hydrochloride (example 138), 38 mg (0.63 mmol) of acetic acid, 43 mg (0.97 mmol) of acetaldehyde, molecular sieves and 515 mg (2.4 mmol) of sodium triacetoxy borohydride in 5 ml of methylene chloride was stirred overnight. The reaction mixture was added to 10 ml of 1 M sodium hydroxide solution and extracted twice with a mixture of methylene chloride and isopropanol. After drying and evaporation 122 mg of 6-(cis-4-diethylamino-cyclohexyloxy)-7-methyl-2H-isoquinolin-1-one (146) were obtained. Rt=0.99 min (Method B). Detected mass: 329.17 (M+H+).

Workup

  1. extractionextracted twice with a mixture of methylene chloride and isopropanol
  2. customAfter drying
  3. customevaporation 122 mg of 6-(cis-4-diethylamino-cyclohexyloxy)-7-methyl-2H-isoquinolin-1-one (146)
  4. customwere obtained

Sources & evidence

ORD record
ord-1e770c31c1e6499489001a3d5e30ec0c
Source dataset
uspto-grants-2014_08
Patent number
US08796458B2

Reaction notes

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