Ethanol → HCID 178496020, compound

HRID 909910Notes

Reaction equation

HRID 909910 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][CH:28]=1)[CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]([N:13]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH2:14][CH:15]([O:18][CH3:19])[O:16][CH3:17])=[O:12])#[N:2].C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:36][OH:37].C(O)C>O>[CH:20]1([N:13]([CH2:14][CH:15]([O:18][CH3:19])[O:16][CH3:17])[C:11](=[O:12])[CH2:10][CH2:9][O:8][CH2:7][CH2:6][C:5]2[CH:26]=[CH:27][CH:28]=[C:3]([C:1](=[NH:2])[NH:36][OH:37])[CH:4]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 581685553-(3-Cyanophenethoxy)-N-cyclohexyl-N-(2,2-dimethoxyethyl)propanamide

Product 1

HCID 178496020HCID 178496020, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

To 3-(3-cyanophenethoxy)-N-cyclohexyl-N-(2,2-dimethoxyethyl)propanamide [Example 10, Step i)] (1.5 g) within a 35 mL microwave vial was added potassium carbonate (0.80 g), hydroxylamine hydrochloride (0.402 g), water (2.5 mL) and ethanol (10 mL). The vial was sealed and stirred for 3 days before being heated at 90° C. for a total of 3 h. The reaction was diluted with water, extracted twice with ethyl acetate, which was pooled and washed twice with water, twice with brine, dried over sodium sulphate, filtered and the solvent removed to afford a colourless gum (1.7 g). This material was used in the next step directly.

Workup

  1. customThe vial was sealed
  2. extractionextracted twice with ethyl acetate, which
  3. washwashed twice with water, twice with brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent removed

Sources & evidence

ORD record
ord-29daa0823a604a05b6700d27bb8df2ec
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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