2-Chlorobenzaldehyde → (R,R)-N-[4-(2-chlorophenyl)-2-butyl]-1-(3-methoxyphenyl)ethylamine

HRID 322575Notes

Reaction equation

HRID 322575 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10](=O)[CH3:11].ClC1C=CC=CC=1C=O.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([C@H:30]([NH2:32])[CH3:31])[CH:27]=[CH:28][CH:29]=1.C([BH3-])#N.[Na+]>C(Cl)(Cl)Cl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C@H:10]([NH:32][C@@H:30]([C:26]1[CH:27]=[CH:28][CH:29]=[C:24]([O:23][CH3:22])[CH:25]=1)[CH3:31])[CH3:11]

Participants

8

Reactant 4

HCID 69962-ChlorobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 7020759(R)-1-(3-Methoxyphenyl)ethylamineHCID 185513004-(2-Chlorophenyl)butan-2-one

Product 1

HCID 54475061(R,R)-N-[4-(2-chlorophenyl)-2-butyl]-1-(3-methoxyphenyl)ethylamine

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

In a similar fashion an equal molar amount of 4-(2-chlorophenyl)-2-butanone, prepared from o-chlorobezaldehyde, (R)-1(3-methoxyphenyl)ethylamine and 1.25 equivalents titanium(IV) isopropoxide were mixed and the intermediate imine reduced with ethanolic sodium cyanoborohydride. Work-up and repetitive preparative thin-layer chromatography using 5% methanol in chloroform afforded (R,R)-N-[4-(2-chlorophenyl)-2-butyl]-1-(3-methoxyphenyl)ethylamine, 4T; m/z (rel. int.) 317 (M+, 3), 302 (16), 178 (62), 135 (100), 125 (15), 105 (10), 91 (6), 77 (8).

Workup

  1. additionwere mixed

Sources & evidence

ORD record
ord-dd215f8e392c43648bdf3b0991076bd9
Source dataset
uspto-grants-2001_04
Patent number
US06211244B1

Reaction notes

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