Acetic Acid → 6-(N-benzyloxycarbonylamino)-2-methylene-hexanal

HRID 376107Notes

Reaction equation

HRID 376107 reaction equation
C=O.N1CCNC[CH2:4]1.C(O)(=O)C.[CH2:13]([O:20][C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]=[O:30])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O>[CH2:13]([O:20][C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28](=[CH2:4])[CH:29]=[O:30])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 4837PiperazineHCID 11391023Benzyl 6-oxohexylcarbamate

Product 1

HCID 189915056-(N-benzyloxycarbonylamino)-2-methylene-hexanal

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.44 g (30 mmol) of 37% aqueous formaldehyde solution are added to a solution of 1.5 g (17 mmol) of anhydrous piperazine and 2.03 g (34 mmol) of acetic acid in 18.7 ml of water. The mixture is stirred at 25° for 15 minutes, and then 7.48 g (30 mmol) of 6-(N-benzyloxycarbonylamino)hexanal are added thereto. The reaction mixture is heated under reflux for 2 hours and then cooled with ice-water and extracted twice with 50 ml of methylene chloride each time. The extracts are combined, washed twice with 25 ml of saturated sodium hydrogen carbonate solution each time and with 25 ml of saturated sodium chloride solution, dried and concentrated to dryness by evaporation. 6-(N-benzyloxycarbonylamino)-2-methylene-hexanal is obtained in the form of a yellowish liquid.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 2 hours
  3. extractionextracted twice with 50 ml of methylene chloride each time
  4. washwashed twice with 25 ml of saturated sodium hydrogen carbonate solution each time
  5. dry with materialwith 25 ml of saturated sodium chloride solution, dried
  6. concentrationconcentrated to dryness by evaporation

Sources & evidence

ORD record
ord-83d43faa82ea4c958bfe346f32f4199a
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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