4-(4-Chloro-3-fluorophenyl)piperidine → (S)-alpha-(2'-(3-(4-(4-chloro-3-fluorophenyl)piperidino)-2-hydroxypropyloxy)benzylidene)-gamma-butyrolactone

HRID 460659Notes

Reaction equation

HRID 460659 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[F:32]>CO>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]2[CH2:27][CH2:28][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])[CH2:30][CH2:31]2)=[CH:22][C:21]=1[F:32]

Participants

4

Reactant 2

HCID 166793134-(4-Chloro-3-fluorophenyl)piperidineHCID 86585643(S)-alpha-(2'-(2,3-epoxypropan-1-yloxy)benzylidene)-gamma-butyrolactone

Product 1

HCID 69901488(S)-alpha-(2'-(3-(4-(4-chloro-3-fluorophenyl)piperidino)-2-hydroxypropyloxy)benzylidene)-gamma-butyrolactoneYield 33.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

By the reaction 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-fluorophenyl)piperidine (0.8 g) in methanol (50 ml), the title compound (0.58 g), melting point 114–115° C.

Sources & evidence

ORD record
ord-319df2f82449400299a54d47a1c90779
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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