Dimethyl Sulfoxide → HCID 68811711, compound

HRID 2403547Notes

Reaction equation

HRID 2403547 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH:17]3[CH2:22][CH2:21][CH:20]([NH:23][C:24](=O)[CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH2:19][CH2:18]3)[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1)#[N:2].CS(C)=[O:33].C(=O)([O-])[O-].[K+].[K+].[H][H]>O>[CH3:29][O:28][CH2:27][CH2:26][CH2:25][CH2:24][NH:23][CH:20]1[CH2:19][CH2:18][CH:17]([CH2:16][CH2:15][N:12]2[CH2:11][CH2:10][N:9]([C:5]3[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=3)[C:1]([NH2:2])=[O:33])[CH2:14][CH2:13]2)[CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 57964842HCID 57964842, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68811711HCID 68811711, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 85 mg (0.2 mmol) of N-(4-{2-[4-(3-cyanophenyl)piperazin-1-yl]ethyl}cyclohexyl)-4-methoxybutanamide, 2 mL of dimethyl sulfoxide, 16.5 mg of potassium carbonate and 0.12 mL of an aqueous 30% hydrogen peroxyde solution is stirred for 2 hours at room temperature. The suspension is poured into 50 mL of water. The solid is filtered, washed with water, dried under reduced pressure to give 15 mg (17%) of 3-(4-{2-[4-(4-methoxybutanylamino)cyclohexyl]ethyl}piperazin-1-yl)benzamide as a white solid.

Workup

  1. filtrationThe solid is filtered
  2. washwashed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-08f625fc99bf49d897662d43fe57fc52
Source dataset
uspto-grants-2014_08
Patent number
US08802678B2

Reaction notes

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