Sodium Hydroxide → N-ethyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine hydrochloride
Reaction equation
[BH4-].[Na+].[Cl:3][C:4]1C=C(C2(C(N)C)CCC2)C=C[C:9]=1Cl.Cl.[Cl:19][C:20]1[CH:21]=[C:22]([C:27]2([CH:31]([NH2:33])[CH3:32])[CH2:30][CH2:29][CH2:28]2)[CH:23]=[CH:24][C:25]=1[Cl:26].[OH-].[Na+]>C(O)(=O)C>[ClH:3].[CH2:4]([NH:33][CH:31]([C:27]1([C:22]2[CH:23]=[CH:24][C:25]([Cl:26])=[C:20]([Cl:19])[CH:21]=2)[CH2:30][CH2:29][CH2:28]1)[CH3:32])[CH3:9]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Sodium borohydride (2.0 g) was added to solution of 1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine (1.5 g prepared by treating the product of Example 1 with aqueous sodium hydroxide) in glacial acetic acid (30 ml). The mixture was heated at 95°-100° C. for sixteen hours and then cooled. Aqueous sodium hydroxide solution was added and the reaction mixture extracted with ether. The ther extract was shaken with 5N hydrochloric acid and the aqueous layer was washed with ether, basified and extracted with ether. Hydrogen chloride gas was passed into the ether extract which was evaporated to dryness. Trituration with acetone gave N-ethyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine hydrochloride (m.p. 211°-212° C.). (Formula I R1 =Me, R2 =H; R3 =Et; R4 =H; R5 =4-Cl and R6 =3- Cl.)
Workup
- customprepared
- temperatureThe mixture was heated at 95°-100° C. for sixteen hours
- temperaturecooled
- extractionthe reaction mixture extracted with ether
- extractionThe ther extract
- washthe aqueous layer was washed with ether
- extractionextracted with ether
- extractionextract which
- customwas evaporated to dryness
Sources & evidence
- ORD record
- ord-1948ace1060c4172bf9bb6a25a251925
- Source dataset
- uspto-grants-1989_03
- Patent number
- US04814352
Reaction notes
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