Sodium hydride → HCID 178511692, compound

HRID 1913115Notes

Reaction equation

HRID 1913115 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]1.[H-].[Na+].Cl.F[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[N:18][CH:17]=[CH:16]2>CC(N(C)C)=O>[CH:19]1[C:20]2[C:15](=[CH:14][C:13]([O:8][C@H:5]3[CH2:6][CH2:7][C@H:2]([NH2:1])[CH2:3][CH2:4]3)=[CH:22][CH:21]=2)[CH:16]=[CH:17][N:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 812934-AminocyclohexanolHCID 67370591HCID 67370591, compound

Product 1

HCID 178511692HCID 178511692, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

6.1 g (53 mmol) of 4-amino-cyclohexanol were dissolved in 50 ml of dimethyl acetamide and 4.24 g (106 mmol) of sodium hydride (60%) were added at room temperature. After the reaction mixture was stirred for 30 minutes under argon, a solution of 6.49 g (35.3 mmol) of 6-fluoro-isoquinoline hydrochloride was added and the mixture was stirred at room temperature overnight. For workup, the solvent was removed in vacuo and the residue was dissolved in dichloromethane and washed twice with water. The organic layer was separated, dried with magnesium sulfate and evaporated to yield 8.64 g of the crude product, which was used without further purification. Rt=0.77 min (Method B). Detected mass: 243.1 (M+H+).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customFor workup, the solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washwashed twice with water
  5. customThe organic layer was separated
  6. dry with materialdried with magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-986c36c575654a7f859c096ecde7493d
Source dataset
uspto-grants-2013_12
Patent number
US08609691B2

Reaction notes

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