Benzyl Alcohol → HCID 57652497, compound

HRID 1930202Notes

Reaction equation

HRID 1930202 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([O:24][C:25]2[CH:26]=[C:27]3[C:32](=[CH:33][CH:34]=2)[C:31](Cl)=[N:30][CH:29]=[CH:28]3)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]>CC(N(C)C)=O>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([O:24][C:25]2[CH:26]=[C:27]3[C:32](=[CH:33][CH:34]=2)[C:31]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:30][CH:29]=[CH:28]3)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 244Benzyl Alcohol2×HCID 24758Sodium hydride2×HCID 57647050HCID 57647050, compound

Product 1

HCID 57652497HCID 57652497, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

0.70 g (6.49 mmol) of benzyl alcohol were dissolved in 10 mL of dimethyl acetamide. 260 mg (6.49 mmol) of sodium hydride (60%) were added and the solution was stirred at room temperature. After 30 min a solution of 1.57 g (4.33 mmol) of 4-(1-chloro-isoquinolin-6-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (10) in 10 mL of dimethyl acetamide was added and the resulting mixture was heated at 90° C. (bath temperature). After 8 h and standing at room temperature overnight 1.0 additional equivalents of benzyl alcohol and sodium hydride were added and heating at 90° C. was continued for 8 h. For workup, the solvent was removed i. vac. and the residue was dissolved in dichloromethane. The organic solution was washed twice with water, dried with MgSO4 and evaporated. The resulting crude product was purified by preparative HPLC. Rt=2.13 min (Method C). Detected mass: 435.2 (M+H+).

Workup

  1. temperaturethe resulting mixture was heated at 90° C. (bath temperature)
  2. waitstanding at room temperature overnight
  3. temperatureheating at 90° C.
  4. waitwas continued for 8 h
  5. customFor workup, the solvent was removed i
  6. dissolutionand the residue was dissolved in dichloromethane
  7. washThe organic solution was washed twice with water
  8. dry with materialdried with MgSO4
  9. customevaporated
  10. customThe resulting crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-058a0e7e4fc14f53a431f751b172e79a
Source dataset
uspto-grants-2012_05
Patent number
US08188117B2

Reaction notes

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