2-Chloro-N,N-dimethylethylamine → 4-(3-Trifluoromethylphenyl)-2,2-dimethyl-7-(2-dimethylaminoethoxy)-1-tetralone

HRID 2059319Notes

Reaction equation

HRID 2059319 reaction equation
FC(F)(F)C1C=C(C2C3C(=CC(OC)=CC=3)C(=O)CC2)C=CC=1.[F:24][C:25]([F:48])([F:47])[C:26]1[CH:27]=[C:28]([CH:32]2[C:41]3[C:36](=[CH:37][C:38]([O:42][CH3:43])=[CH:39][CH:40]=3)[C:35](=[O:44])[C:34]([CH3:46])([CH3:45])[CH2:33]2)[CH:29]=[CH:30][CH:31]=1.CI.CC(C)([O-])C.[K+].[CH3:57][N:58]([CH2:60]CCl)[CH3:59]>C(O)(C)(C)C>[F:24][C:25]([F:47])([F:48])[C:26]1[CH:27]=[C:28]([CH:32]2[C:41]3[C:36](=[CH:37][C:38]([O:42][CH2:43][CH2:57][N:58]([CH3:60])[CH3:59])=[CH:39][CH:40]=3)[C:35](=[O:44])[C:34]([CH3:45])([CH3:46])[CH2:33]2)[CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 79012-Chloro-N,N-dimethylethylamineHCID 205458954-(3-Trifluoromethylphenyl)-7-methoxy-2,2-dimethyl-1-tetraloneHCID 205459114-(3-Trifluoromethylphenyl)-7-methoxy-1-tetraloneHCID 23692030Methyl iodide potassium t-butoxide

Product 1

HCID 205459264-(3-Trifluoromethylphenyl)-2,2-dimethyl-7-(2-dimethylaminoethoxy)-1-tetralone

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

4-(3-Trifluoromethylphenyl)-7-methoxy-1-tetralone was converted to 4-(3-trifluoromethylphenyl)-7-methoxy-2,2-dimethyl-1-tetralone using methyl iodide-potassium t-butoxide in t-butanol (88%). Dimethylation and alkylation with dimethylaminoethylchloride, as described above, gave 4-(3-trifluoromethylphenyl)-2,2-dimethyl-7-(2-dimethylaminoethoxy)-1-tetralone, obtained, after purification by chromatography on alumina with ether-light petrol (b.p. 60°-80°), as a brown oil (40%). A portion was converted to the hydrochloride salt (92%) which formed white prisms from ethanol-ether, m.p. 208°-209°.

Sources & evidence

ORD record
ord-fd10f628ce6e4431b0de3f4a5224f565
Source dataset
uspto-grants-1982_03
Patent number
US04322370

Reaction notes

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