4-Methylbenzaldehyde → HCID 3042115, compound

HRID 704391Notes

Reaction equation

HRID 704391 reaction equation
[BH4-].[Na+].[N:3]1([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[C:14]1([CH3:22])[CH:19]=[CH:18][C:17]([CH:20]=O)=[CH:16][CH:15]=1>C(O)C>[C:14]1([CH3:22])[CH:19]=[CH:18][C:17]([CH2:20][N:6]2[CH2:7][CH2:8][N:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][CH2:5]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 77254-MethylbenzaldehydeHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 4311764Sodium borohydride

Product 1

HCID 3042115HCID 3042115, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (500 mg) was added to a mixture of 1.6 g of ethyl 1-piperazinecarboxylate, 1.3 g of p-tolualdehyde and 30 ml of ethanol, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, 50 ml of water was added, and the resultant mixture was extracted with ethyl acetate. The ethyl acetate extract was then extracted with diluted hydrochloric acid. The diluted hydrochloric acid extract was washed with ethyl acetate, made alkaline with sodium hydrogen carbonate and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous potassium carbonate and concentrated under reduced pressure to give 0.8 g of ethyl 4-p-tolylmethyl-1-piperazinecarboxylate as an oil. This was deprived of the carboethoxy group by the method described in Reference Example 38 to give 0.36 g of 1-ptolylmethylpiperazine as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, 50 ml of water
  2. additionwas added
  3. extractionthe resultant mixture was extracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. extractionwas then extracted with diluted hydrochloric acid
  6. extractionThe diluted hydrochloric acid extract
  7. washwas washed with ethyl acetate
  8. extractionextracted with ethyl acetate
  9. washThe extract was washed with water
  10. dry with materialdried over anhydrous potassium carbonate
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-565e2f7f0773430faa34b36121d557ea
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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