Acetyl chloride → HCID 178475033, compound

HRID 2402576Notes

Reaction equation

HRID 2402576 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C@H:12]3[CH2:17][CH2:16][C@H:15]([NH2:18])[CH2:14][CH2:13]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[C:19](Cl)(=[O:21])[CH3:20]>ClCCl.N1C=CC=CC=1.ClCCl>[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C@H:12]3[CH2:13][CH2:14][C@H:15]([NH:18][C:19](=[O:21])[CH3:20])[CH2:16][CH2:17]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 178511692HCID 178511692, compound

Product 1

HCID 178475033HCID 178475033, compoundYield 45.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21875418Pyridine methylene chlorideSolvent

Procedure

8.4 g (34.7 mmol) of 4-(isoquinolin-6-yloxy)-cyclohexylamine (15) were dissolved in 100 ml of dichloromethane/pyridine (4:1). At 0° C. a solution of 3.27 g (41.6 mmol) of acetyl chloride in 10 ml of dichloromethane was added and the reaction mixture was stirred at room temperature. After 2 h, the solution was diluted with dichloromethane and washed twice with saturated sodium bicarbonate solution. After washing twice with 2 N HCl, the product was transferred to the aqueous phase. The HCl-layers were adjusted to alkaline pH by addition of solid NaOH and extracted three times with dichloromethane. Drying the organic layers with magnesium sulfate and evaporation of the solvent gave 7.69 g of the crude product. After silica gel chromatography 4.48 g of the title compound were isolated. Rt=0.87 min (Method A). Detected mass: 285.2 (M+H+).

Workup

  1. washwashed twice with saturated sodium bicarbonate solution
  2. washAfter washing twice with 2 N HCl
  3. additionby addition of solid NaOH
  4. extractionextracted three times with dichloromethane
  5. customDrying the organic layers
  6. customwith magnesium sulfate and evaporation of the solvent
  7. customgave 7.69 g of the crude product

Sources & evidence

ORD record
ord-84c605d8f84946a2a675930860f40751
Source dataset
uspto-grants-2014_08
Patent number
US08796458B2

Reaction notes

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