4-[4-Chloro-3-(trifluoromethyl)phenyl]piperidine → (S)-alpha-(2'-(3-(4-(4-chloro-3-trifluoromethylphenyl)piperidino)-2-hydroxypropyloxy) benzylidene)-gamma-butyrolactone Hydrochloride Monohydrate

HRID 460660Notes

Reaction equation

HRID 460660 reaction equation
[O:1]1[CH2:18][C@H:2]1[CH2:3][O:4][C:5]1[CH:17]=[CH:16][CH:15]=[CH:14][C:6]=1[CH:7]=[C:8]1[CH2:13][CH2:12][O:11][C:9]1=[O:10].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:22][C:21]=1[C:32]([F:35])([F:34])[F:33].CO.Cl>CO>[OH2:1].[ClH:19].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]2[CH2:31][CH2:30][N:29]([CH2:18][C@H:2]([OH:1])[CH2:3][O:4][C:5]3[CH:17]=[CH:16][CH:15]=[CH:14][C:6]=3[CH:7]=[C:8]3[CH2:13][CH2:12][O:11][C:9]3=[O:10])[CH2:28][CH2:27]2)=[CH:22][C:21]=1[C:32]([F:35])([F:33])[F:34]

Participants

5

Reactant 3

HCID 166793174-[4-Chloro-3-(trifluoromethyl)phenyl]piperidineHCID 21893726Hydrochloride methanolHCID 86585643(S)-alpha-(2'-(2,3-epoxypropan-1-yloxy)benzylidene)-gamma-butyrolactone

Product 1

HCID 69497791(S)-alpha-(2'-(3-(4-(4-chloro-3-trifluoromethylphenyl)piperidino)-2-hydroxypropyloxy) benzylidene)-gamma-butyrolactone Hydrochloride MonohydrateYield 52.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The reaction was performed in same manner as in Example 307 using (S)-α-(2′-(2,3-epoxypropan-1-yloxy)benzylidene)-γ-butyrolactone (1.0 g) and 4-(4-chloro-3-trifluoromethylphenyl)piperidine (0.8 g) in methanol (50 ml), and the obtained oil was treated with methanol/hydrochloric acid to give the title compound (0.45 g), melting point 172–174° C.

Sources & evidence

ORD record
ord-f0ef088f4f2049c3943f949991cc5401
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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