Formic Acid → HCID 13083334, compound

HRID 325871Notes

Reaction equation

HRID 325871 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:12][C:13](=O)[CH3:14])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(O)=O.C([NH2:21])=O.Cl>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:12][CH:13]([NH2:21])[CH3:14])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 713FormamideHCID 13083375HCID 13083375, compound

Product 1

HCID 13083334HCID 13083334, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 1-[1-(4-chlorophenyl)cyclobutyl]propan-2-one prepared as described in Example 3 (15 g) and 98% formic acid (4 ml) was added dropwise to formamide (12 ml) at 160° C. The temperature was raised to 180° C. and maintained at this temperature for ten hours. The mixture was cooled, diluted with water and extracted with dichloromethane. The extract was washed, dried and evaporated to yield a yellow oil which was hydrolysed with concentrated hydrochloric acid under reflux. The resulting aqueous solution after dilution with water was washed with ether, aqueous NaOH was added and the aqueous solution extracted with ether. The extracts were washed, dried and evaporated to yield a residue which on distillation gave 2-[1-(4-chlorophenyl)cyclobutyl]-1-methylethylamine (b.p. 105°-107°/0.7 mm Hg).

Workup

  1. customprepared
  2. temperaturemaintained at this temperature for ten hours
  3. temperatureThe mixture was cooled
  4. extractionextracted with dichloromethane
  5. washThe extract was washed
  6. customdried
  7. customevaporated
  8. customto yield a yellow oil which
  9. temperatureunder reflux
  10. washThe resulting aqueous solution after dilution with water was washed with ether, aqueous NaOH
  11. additionwas added
  12. extractionthe aqueous solution extracted with ether
  13. washThe extracts were washed
  14. customdried
  15. customevaporated
  16. customto yield a residue which
  17. distillationon distillation

Sources & evidence

ORD record
ord-5c9e4e88b4b44a699ef804096466728c
Source dataset
uspto-grants-1984_04
Patent number
US04443449

Reaction notes

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