2-Chloroacetophenone → N-[3-methyl-3-(2-chlorophenyl)propyl]-1-(3-methoxyphenyl)ethylamine

HRID 322593

Reaction equation

HRID 322593 reaction equation
ClCC(C1C=CC=CC=1)=O.CC1(C2C=CC=CC=2Cl)C=CC=C(C=CC#N)C1.[2H][2H].[CH3:31][CH:32]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[Cl:42])[CH2:33][CH2:34][NH2:35].[CH3:43][O:44][C:45]1[CH:46]=[C:47]([C:51](=O)[CH3:52])[CH:48]=[CH:49][CH:50]=1.C([BH3-])#N.[Na+]>[OH-].[Pd+2].[OH-].CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C(O)(=O)C>[CH3:31][CH:32]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[Cl:42])[CH2:33][CH2:34][NH:35][CH:51]([C:47]1[CH:48]=[CH:49][CH:50]=[C:45]([O:44][CH3:43])[CH:46]=1)[CH3:52]

Participants

10

Reactant 6

HCID 107572-ChloroacetophenoneHCID 114603-MethoxyacetophenoneHCID 24523DeuteriumHCID 5003444Sodium cyanoborohydrideHCID 220110753-(2-Chlorophenyl)butan-1-amineHCID 697099713-Methyl-3-(2-chlorophenyl)cinnamonitrile

Product 1

HCID 22011056N-[3-methyl-3-(2-chlorophenyl)propyl]-1-(3-methoxyphenyl)ethylamine

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

In a similar fashion, 2-chloroacetophenone was used to prepare 3-methyl-3-(2-chlorophenyl)cinnamonitrile. The nitrile was catalytically reduced (palladium hydroxide, acetic acid, 60 p.s.i. hydrogen 2 hr) to generate 3-methyl-3-(2-chlorophenyl)propylamine. An equal molar amount of the amine, 3′-methoxyacetophenone and 1.25 molar equivalents titanium(IV) isopropoxide were mixed 4 hr at rt and the intermediate imine treated with an ethanolic sodium cyanoborohydride (5 ml of 1 M, 5 mmol). Work-up and chromatography afforded N-[3-methyl-3-(2-chlorophenyl)propyl]-1-(3-methoxyphenyl)ethylamine, 4Y, as an oil; m/z (rel. int.) 283 (M+, 17), 268 (71), 164 (13), 135 (100), 121 (21), 105 (27), 91 (26), 77 (14).

Sources & evidence

ORD record
ord-b790e942ceba4fab839c4257a694ce62
Source dataset
uspto-grants-2001_04
Patent number
US06211244B1

Linked notes

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