Dimethylformamide → HCID 21187559, compound

HRID 1383333Notes

Reaction equation

HRID 1383333 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH:10]=[C:11]([CH3:17])[NH:12]3)[CH2:4][CH2:3]1.O(Cl)Cl.[OH-].[Na+].CN(C)[CH:25]=[O:26]>>[CH:25]([C:10]1[C:9]2[C:13](=[CH:14][CH:15]=[CH:16][C:8]=2[N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)[NH:12][C:11]=1[CH3:17])=[O:26]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24646Chlorine monoxideHCID 15550247HCID 15550247, compound

Product 1

HCID 21187559HCID 21187559, compoundYield 22%

Procedure

To a stirred solution of 4-methyl-1-(2-methyl-1H-indol-4-yl)piperazine (0.247 g, 1.08 mmol) in anhydrous N,N-dimethylformamide (1 mL) at 0° C. was added dropwise a solution of phorsphorus oxychloride (0.16 g, 1.04 mmol) in anhydrous N,N-dimethylformamide (1 mL). The resulting reaction solution was stirred at room temperature under nitrogen for 2 hours. An aqueous solution of sodium hydroxide (10% by weight, 3 mL) was then added, and the resulting solution was stirred at room temperature under nitrogen overnight. The reaction solution was then evaporated under reduced pressure, and the residue was chromatographed using silica gel (approximately 50 g) and elution with methylene chloride/methanol/ammonium hydroxide [10:1:0.1] to afford the title compound (0.060 g, 0.23 mmol, 22%) as an off-white foam: 1H NMR (DMSO-d6) δ12.14 (br s, NH), 10.46 (s, 1H), 7.14-7.08 (m, 2H), 6.88 (dd, J=1.4 and 7.1 Hz, 1H), 3.11 (br m, 8H), 2.66 (s, 3H); FAB LRMS (m/z, relative intensity) 259 (16), 258 (MH+, 100).

Workup

  1. customThe resulting reaction solution
  2. stirringthe resulting solution was stirred at room temperature under nitrogen overnight
  3. customThe reaction solution was then evaporated under reduced pressure
  4. customthe residue was chromatographed
  5. washsilica gel (approximately 50 g) and elution with methylene chloride/methanol/ammonium hydroxide [10:1:0.1]

Sources & evidence

ORD record
ord-0b26594386be426289cb52ace7defa8c
Source dataset
uspto-grants-2001_07
Patent number
US06255306B1

Reaction notes

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