Hydrochloric Acid → HCID 66887153, compound

HRID 2063735Notes

Reaction equation

HRID 2063735 reaction equation
[CH3:1][NH:2][CH3:3].Cl.[CH2:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][N:6]1[CH2:14][CH:15]([CH:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1)[OH:16].[C-:24]#[N:25].[K+]>CO.O1CCCC1.O>[CH2:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][N:6]1[CH2:14][CH:15]([CH:17]1[CH2:22][CH2:21][C:20]([N:2]([CH3:3])[CH3:1])([C:24]#[N:25])[CH2:19][CH2:18]1)[OH:16]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 9032Potassium CyanideHCID 66887506HCID 66887506, compound

Product 1

HCID 66887153HCID 66887153, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

40% aqueous dimethylamine solution (1.72 ml, 12.5 mmol) was added to 4 M hydrochloric acid (706 μl), cooled to 0, in methanol (785 μl). A solution of 4-[2-(1,3-dihydroisoindol-2-yl)-1-hydroxyethyl]cyclohexanone (732 mg, 2.82 mmol) in methanol (4 ml) and tetrahydrofuran (6 ml) was then added. Potassium cyanide (445 mg, 6.67 mmol) was then added to the mixture and the mixture was stirred at room temperature overnight. Thereafter, water (80 ml) was added to the reaction mixture and the mixture was extracted with diethyl ether (3×20 ml). The combined organic phases were dried with sodium sulfate and concentrated in vacuo.

Workup

  1. extractionthe mixture was extracted with diethyl ether (3×20 ml)
  2. dry with materialThe combined organic phases were dried with sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-42f6e75ff00c4b77a154f308a078d90c
Source dataset
uspto-grants-2012_10
Patent number
US08288406B2

Reaction notes

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