Hydrochloric Acid → n,n-Dimethyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]butylamine hydrochloride
Reaction equation
[CH:1]([NH:3][CH:4]([C:8]1([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[CH2:11][CH2:10][CH2:9]1)[CH2:5][CH2:6][CH3:7])=O.[CH3:20]COCC.Cl.C=O>CC(O)C.C(O)=O.O>[ClH:18].[CH3:1][N:3]([CH:4]([C:8]1([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[CH2:11][CH2:10][CH2:9]1)[CH2:5][CH2:6][CH3:7])[CH3:20]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
The product of Example 7 (8.3 g), diethyleneglycoldimethyl ether (50 ml), water (20 ml) and concentrated hydrochloric acid (20 ml) were mixed and heated under reflux for sixteen hours. The mixture was poured into water aqueous NaOH was added and the product extracted into ether. Evaporation gave a dark oil. A sample of this oil (7.9 g), water (0.7 ml) and formic acid (6.5 ml) were mixed and formaldehyde (6.5 ml) added. The mixture was heated under reflux for three hours and then concentrated hydrochloric acid (10 ml) and propan-2-ol (10 ml) were added. Evaporation to dryness gave N,N-dimethyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]butylamine hydrochloride (m.p. 195°-196°) as a white solid (Formula I R1 =propyl; R2 =H; R3, R4 =Me; R5 =4-Cl and R6 =3-Cl).
Workup
- temperatureheated
- temperatureunder reflux for sixteen hours
- additionwas added
- extractionthe product extracted into ether
- customEvaporation
- customgave a dark oil
- temperatureThe mixture was heated
- temperatureunder reflux for three hours
- customEvaporation to dryness
Sources & evidence
- ORD record
- ord-d33725e3d1794c86a56465e7c4184822
- Source dataset
- uspto-grants-1988_05
- Patent number
- US04746680
Reaction notes
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