Formic Acid → 1-[1-(3,4-Dichlorophenyl)cyclobutyl]ethylamine
Reaction equation
[C:1]([C:4]1([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[CH2:7][CH2:6][CH2:5]1)(=O)[CH3:2].C([NH2:18])=O.C(O)=O.Cl>C(NC(C1(C2C=CC(Cl)=C(Cl)C=2)CCC1)C)=O>[Cl:15][C:10]1[CH:9]=[C:8]([C:4]2([CH:1]([NH2:18])[CH3:2])[CH2:7][CH2:6][CH2:5]2)[CH:13]=[CH:12][C:11]=1[Cl:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 180 °C
Procedure
The 1-acetyl-1-(3,4-dichlorophenyl)cyclobutane (9,1 g) prepared above, formamide (6.5 ml) and 98% formic acid (3 ml) were heated at 180° C. for 16 hours to result in N-formyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine. Concentrated hydrochloric acid (20 ml) was added, and the mixture was refluxed for 3 hours. The solution was then cooled and washed with ether, and sodium hydroxide solution was added. The product was extracted with ether, and the ether extract was washed with water, dried and evaporated. 1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine was isolated by distillation (boiling point: 112 to 118° C. under 0.27 mbar). The amine was dissolved in 2-propanol and concentrated hydrochloric acid, and the solution was evaporated to dryness to result in 1-[1-(3,4-dichlorophenyl)cyclobutyl]-ethylamine.hydrochloride (melting point: 185 to 195° C.). (Formula III: n=0; R1 =methyl; R2, R3 and R4 =H; R5 =4-Cl; R6 =3-Cl).
Workup
- temperaturethe mixture was refluxed for 3 hours
- temperatureThe solution was then cooled
- washwashed with ether, and sodium hydroxide solution
- additionwas added
- extractionThe product was extracted with ether
- extractionthe ether extract
- washwas washed with water
- customdried
- customevaporated
Sources & evidence
- ORD record
- ord-cd6ee8efb3684bc1bd151c0b565cd0de
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06127424
Reaction notes
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