Formic Acid → N-formyl-1-[1-(4-chlorophenyl)cyclobutyl]butylamine

HRID 1248131Notes

Reaction equation

HRID 1248131 reaction equation
[C:1]([C:6]1([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH2:9][CH2:8][CH2:7]1)(=O)[CH2:2][CH2:3][CH3:4].C(O)=O.[CH:20]([NH2:22])=[O:21]>CCOCC>[CH:20]([NH:22][CH:1]([C:6]1([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH2:9][CH2:8][CH2:7]1)[CH2:2][CH2:3][CH3:4])=[O:21]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 713FormamideHCID 130833671-Butyryl-1-(4-chlorophenyl)cyclobutane

Product 1

HCID 13083181N-formyl-1-[1-(4-chlorophenyl)cyclobutyl]butylamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of the ketone produced as described above (21 g) and 98% formic acid (6 ml) was added over a period of one and a half hours to formamide (15 ml) at 160° C. After completion of the addition the temperature was raised to 180° to 185° C. and maintained in this range for five hours. The mixture was cooled and extracted with chloroform to yield a thick gum which on heating with petroluem ether (b.p. 60°-80°) gave a colourless solid which was recrystallised from petroleum ether (b.p. 60°-80°) to yield N-formyl-1-[1-(4-chlorophenyl)cyclobutyl]butylamine (m.p. 97.5° to 98.5° C.) (Formula I R1 =propyl; R2 =H; R3 =H; R4 =CHO; R5 =4-Cl; R6 =H).

Workup

  1. customproduced
  2. additionAfter completion of the addition the temperature
  3. temperaturewas raised to 180° to 185° C.
  4. temperaturemaintained in this range for five hours
  5. temperatureThe mixture was cooled
  6. extractionextracted with chloroform
  7. customto yield a thick gum which
  8. customgave a colourless solid which
  9. customwas recrystallised from petroleum ether (b.p. 60°-80°)

Sources & evidence

ORD record
ord-8b99827c8ca94311a732c0aee0925076
Source dataset
uspto-grants-1985_06
Patent number
US04522828

Reaction notes

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