Ethanol → HCID 58994654, compound

HRID 606317Notes

Reaction equation

HRID 606317 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:22])=[C:5]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH:20]=O)=[CH:12][N:11]=2)[C:6]([CH3:9])=[CH:7][CH:8]=1.[NH:23]1[C:27]2C=CC=C[C:26]=2N=N1.CCO.[CH2:35]([Mg]Cl)[CH2:36][CH3:37].[C:40]1([CH3:46])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>O>[CH2:46]([N:23]([CH2:27][CH3:26])[CH:20]([C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]([C:5]2[C:6]([CH3:9])=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=2[CH3:22])=[N:11][CH:12]=1)[CH2:35][CH2:36][CH3:37])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

7

Reactant 5

HCID 702EthanolHCID 1140TolueneHCID 87247801HCID 87247801, compoundHCID 178418385HCID 178418385, compoundHCID 178455855HCID 178455855, compound

Product 1

HCID 58994654HCID 58994654, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of the aldehyde from Step 1 (115 mg, 0.39 mmol), benzotriazole (50 mg, 0.41 mmol), and EtOH (0.5 ml) in toluene (8 ml) is heated to reflux for 2 h under a Dean-Stark water trap. The solvents are removed completely by using IR-Dancer and the residue is dissolved in THF (6 ml). After cooling to 0° C., n-PrMgCl (0.3 ml of 2M solution in Et2O, 0.59 mmol) is added slowly and the mixture is stirred for 15 min at ambient temperature. Water is added and the mixture is extracted with EtOAc. The combined extracts are dried over Na2SO4 and concentrated. The residue is chromatographed on silica gel to give 130 mg of benzyl-ethyl-{1-[1-(3-methoxy-2,6-dimethyl-phenyl)-isoquinolin-4-yl]-butyl}-amine as a colorless oil.

Workup

  1. temperatureis heated
  2. customThe solvents are removed completely
  3. dissolutionthe residue is dissolved in THF (6 ml)
  4. extractionthe mixture is extracted with EtOAc
  5. dry with materialThe combined extracts are dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-c1d6ee8187324eb8a5458746fcdfa320
Source dataset
uspto-grants-2011_03
Patent number
US07915288B2

Reaction notes

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