Phenylacetaldehyde → 4-(4-Acetamido-4-phenylpiperidino)-2-(3,4-dichlorophenyl)-N-phenethyl-N-[3,5-bis(trifluoromethyl)benzyl]butylamine

HRID 613786Notes

Reaction equation

HRID 613786 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH2:9][CH2:10]CCN)[CH:5]=[CH:6][C:7]=1Cl.FC(F)(F)C1C=C(C=C(C(F)(F)F)C=1)C=O.[C:30]([NH:33][C:34]1([C:68]2[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=2)[CH2:39][CH2:38][N:37]([CH:40]([CH2:53][C:54]2[CH:59]=[C:58]([C:60]([F:63])([F:62])[F:61])[CH:57]=[C:56]([C:64]([F:67])([F:66])[F:65])[CH:55]=2)[CH2:41][CH:42]([C:45]2[CH:50]=[CH:49][C:48]([Cl:51])=[C:47]([Cl:52])[CH:46]=2)[CH2:43][NH2:44])[CH2:36][CH2:35]1)(=[O:32])[CH3:31].C1(CC=O)C=CC=CC=1>CO.ClCCl>[C:30]([NH:33][C:34]1([C:68]2[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=2)[CH2:35][CH2:36][N:37]([CH:40]([CH2:53][C:54]2[CH:55]=[C:56]([C:64]([F:65])([F:66])[F:67])[CH:57]=[C:58]([C:60]([F:62])([F:61])[F:63])[CH:59]=2)[CH2:41][CH:42]([C:45]2[CH:50]=[CH:49][C:48]([Cl:51])=[C:47]([Cl:52])[CH:46]=2)[CH2:43][NH:44][CH2:10][CH2:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=2)[CH2:38][CH2:39]1)(=[O:32])[CH3:31]

Participants

7

Reactant 4

HCID 998PhenylacetaldehydeHCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 235442224-(3,4-Dichlorophenyl)butan-1-amineHCID 570149314-(4-Acetamido-4-phenylpiperidino)-2-(3,4-dichlorophenyl)-N-[3,5-bis(trifluoromethyl)benzyl]butylamine

Product 1

HCID 867549924-(4-Acetamido-4-phenylpiperidino)-2-(3,4-dichlorophenyl)-N-phenethyl-N-[3,5-bis(trifluoromethyl)benzyl]butylamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Using a procedure similar to that described in Example 1, except replacing the (3,4-dichlorophenyl)butylamine and the 3,5-bis(trifluoromethyl)benzaldehyde used therein with 4-(4-acetamido-4-phenylpiperidino)-2-(3,4-dichlorophenyl)-N-[3,5-bis(trifluoromethyl)benzyl]butylamine and phenylacetaldehyde, respectively, the title compound was prepared; mp 55-57° C.; partial NMR (DMSO): 7.1-6.95 (broad m,11), 3.88 (d,1), 3.65 (d,1), 3.35(d,1), 3.15(d,1), 1.85 (s,3); MS: m/z=764(M+1,100%); TLC: Rf=0.44 (10:1 dichloromethane:methanol). Analysis for C40H41Cl2F6N3O: Calculated: C, 62.83; H, 5.40; N, 5.50; Found: C, 63.18; H, 5.71; N, 5.35.

Sources & evidence

ORD record
ord-8f579f03601946ce8d2613df1d36e288
Source dataset
uspto-grants-1999_12
Patent number
US06008223

Reaction notes

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