Sodium Hydroxide → HCID 86639102, compound

HRID 1260368Notes

Reaction equation

HRID 1260368 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:11]([N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].CO[CH:22](OC)[N:23]([CH3:25])[CH3:24].N1CC[CH2:30][CH2:29]1.[OH-].[Na+]>CN(C)C=O>[CH3:19][N:16]1[CH2:15][CH2:14][N:13]([C:11]([C:4]2[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([CH:1]=[CH:25][N:23]3[CH2:22][CH2:30][CH2:29][CH2:24]3)[CH:3]=2)=[O:12])[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 31268PyrrolidineHCID 78373Dimethylformamide dimethyl acetalHCID 718014(3-Methyl-4-nitrophenyl)-(4-methylpiperazin-1-yl)methanone

Product 1

HCID 86639102HCID 86639102, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(3-Methyl-4-nitrophenyl)-(4-methylpiperazin-1-yl)methanone (3.8022 mmol, 1.0 grams) (obtained from, step (i)) was taken in a 25 mL two necked round bottomed flask attached with a condenser, under nitrogen atmosphere. To this, was added 3 mL of N,N-dimethylformamide, N,N-dimethylformamide dimethylacetal (5.7033 mmol) and pyrrolidine (5.7033 mmol) and refluxed for a period of 6 hours. After the completion of reaction, the reaction mixture was poured on to 20 grams of ice water, basified with 20% NaOH solution (pH to 10) and the mixture was extracted with ethyl acetate (2×30 mL). The combined ethyl acetate extracts were then washed with water (2×30 mL), brine (30 mL) and dried over anhydrous sodium sulfate. The volatiles were removed under reduced pressure to obtain thick syrupy mass. This thick syrupy mass was used for the next step of the reaction without purification.

Workup

  1. customattached with a condenser, under nitrogen atmosphere
  2. temperaturerefluxed for a period of 6 hours
  3. customAfter the completion of reaction
  4. extractionthe mixture was extracted with ethyl acetate (2×30 mL)
  5. washThe combined ethyl acetate extracts were then washed with water (2×30 mL), brine (30 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe volatiles were removed under reduced pressure
  8. customto obtain thick syrupy mass
  9. customThis thick syrupy mass was used for the next step of the reaction without purification

Sources & evidence

ORD record
ord-ed151342cd404935bd514a067834592b
Source dataset
uspto-grants-2013_06
Patent number
US08470830B2

Reaction notes

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