Sodium Hydroxide → HCID 18352964, compound

HRID 429846Notes

Reaction equation

HRID 429846 reaction equation
[O-:1][C:2]#[N:3].[K+].[NH2:5][C:6]1[CH:7]=[C:8]([CH2:12][CH:13]([N:15]([CH2:19][CH:20]2[CH2:25][CH2:24][N:23]([S:26]([CH3:29])(=[O:28])=[O:27])[CH2:22][CH2:21]2)[CH2:16][CH2:17][CH3:18])[CH3:14])[CH:9]=[CH:10][CH:11]=1.[OH-].[Na+]>O.C(O)(=O)C>[C:2]([NH:5][C:6]1[CH:7]=[C:8]([CH2:12][CH:13]([N:15]([CH2:19][CH:20]2[CH2:25][CH2:24][N:23]([S:26]([CH3:29])(=[O:28])=[O:27])[CH2:22][CH2:21]2)[CH2:16][CH2:17][CH3:18])[CH3:14])[CH:9]=[CH:10][CH:11]=1)(=[O:1])[NH2:3]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 11378442Potassium cyanateHCID 18352740HCID 18352740, compound

Product 1

HCID 18352964HCID 18352964, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of potassium cyanate (9 mg) in water (0.5 ml) was added to a solution of N-[2-(3-aminophenyl)-1-methylethyl]-N-propyl-(1-methanesulfonylpiperidin-4-ylmethyl)amine (40 mg) in water (2 ml) and acetic acid (1 ml). The mixture was stirred at ambient temperature for about 72 hours and then basified to pH 9 with 10% sodium hydroxide. The solution was extracted with dichloromethane, and the organic phase dried over sodium sulfate, filtered, evaporated in vacuo to give N-[2-(3-carbamoylaminophenyl)-1-methylethyl]-N-propyl-(1-methanesulfonylpiperidin-4-ylmethyl)amine (35 mg), M+H 411.2

Workup

  1. extractionThe solution was extracted with dichloromethane
  2. dry with materialthe organic phase dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-c3bbc51d921245f5a8e688f6b62b82b1
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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