Formic Acid → N-isopropyl-1-[1-(4-chlorophenyl)cyclobutyl]ethylamine hydrochloride

HRID 35703Notes

Reaction equation

HRID 35703 reaction equation
C(C1(C2C=CC([Cl:14])=CC=2)CCC1)(=O)C.[C:15]([C:18]1([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24](Cl)[CH:23]=2)[CH2:21][CH2:20][CH2:19]1)(=O)[CH3:16].C(O)=O.[CH:33]([NH:36]C=O)([CH3:35])[CH3:34]>Cl>[ClH:14].[CH:33]([NH:36][CH:15]([C:18]1([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH2:21][CH2:20][CH2:19]1)[CH3:16])([CH3:35])[CH3:34]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 268118N-(propan-2-yl)formamideHCID 130831391-Acetyl-1-(3,4-dichlorophenyl)cyclobutaneHCID 212584081-[1-(4-Chlorophenyl)cyclobutyl]ethanone

Product 1

HCID 13083297N-isopropyl-1-[1-(4-chlorophenyl)cyclobutyl]ethylamine hydrochloride

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Conditions

Temperature
180 °C

Procedure

1-Acetyl-1-(4-chlorophenyl)cyclobutane (10.4 g) prepared in a similar manner to that described in Example 1 for 1-acetyl-1-(3,4-dichlorophenyl)cyclobutane and 98% formic acid (5 ml) were added to N-isopropylformamide (43.5 g) and the mixture heated at 180° C. for four hours. Excess starting material was distilled off under reduced pressure (20 mm Hg) to leave a viscous residue which was heated under reflux with concentrated hydrochloric acid (30 ml) for six hours. The reaction mixture was washed with ether until a colourless solution was obtained. The aqueous phase was basified, extracted with ether, dried and evaporated to give an oil which was dissolved in 5N hydrochloric acid. On evaporation a yellow oil was obtained which was triturated with petroleum ether (b.p. 62°-68° C.) to give N-isopropyl-1-[1-(4-chlorophenyl)cyclobutyl]ethylamine hydrochloride (m.p. 170°-174° C.) (Formula I R1 =Me; R2 =H; R3 =isopropyl; R4 =H; R5 =4--Cl; R6 =H).

Workup

  1. distillationwas distilled off under reduced pressure (20 mm Hg)
  2. customto leave a viscous residue which
  3. temperaturewas heated
  4. washThe reaction mixture was washed with ether until a colourless solution
  5. customwas obtained
  6. extractionextracted with ether
  7. customdried
  8. customevaporated
  9. customto give an oil which
  10. customOn evaporation a yellow oil
  11. customwas obtained which
  12. customwas triturated with petroleum ether (b.p. 62°-68° C.)

Sources & evidence

ORD record
ord-76e02134eee448abbe7a63bc5281899e
Source dataset
uspto-grants-1988_08
Patent number
US04767790

Reaction notes

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