1-Methylpiperazine → 1-(2-Chlorodibenzo[b,f]oxepin-10-yl)-4-methylpiperazine

HRID 1448464Notes

Reaction equation

HRID 1448464 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9](=O)[CH2:10][C:4]=2[CH:3]=1.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9]([N:22]3[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]3)=[CH:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 521998p-Toluenesulfonic acid monohydrateHCID 127651152-Chlorodibenzo[b,f]oxepin-10(11h)-one

Product 1

HCID 127651161-(2-Chlorodibenzo[b,f]oxepin-10-yl)-4-methylpiperazineYield 79.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Thirty grams of 2-chlorodibenzo[b,f]oxepin-10(11H)-one, prepared in accordance with the procedure of Example 3, 45 grams of N-methylpiperazine and a solution of 8 grams of p-toluenesulfonic acid monohydrate in 150 ml of xylene are refluxed for a period of 22 hours in a reflux apparatus equipped with a Dean-Stark trap in order to remove the water that forms. The reaction mixture is cooled, treated with a solution of sodium bicarbonate, washed with water until the water washings are neutral, dried over anhydrous sodium sulfate and filtered through a column of neutral aluminum oxide. The filtrate is concentrated to dryness in vacuo and the residue, 46 grams, crystallized from ethanol to yield 32 grams of 1-(2-chlorodibenzo[b,f]oxepin-10-yl)-4-methylpiperazine having an m.p. of 119°-121° C.

Workup

  1. customequipped with a Dean-Stark trap in order
  2. customto remove the water that forms
  3. temperatureThe reaction mixture is cooled
  4. additiontreated with a solution of sodium bicarbonate
  5. washwashed with water until the water washings
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered through a column of neutral aluminum oxide
  8. concentrationThe filtrate is concentrated to dryness in vacuo
  9. customthe residue, 46 grams, crystallized from ethanol

Sources & evidence

ORD record
ord-c5c579daf7f9466dada37c1d4dd840c3
Source dataset
uspto-grants-1979_12
Patent number
US04180559

Reaction notes

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