Hydrochloric Acid → 6-{(S)-1-[(3S,4S)-3-(4-Chloro-phenyl)-piperidin-4-yl]-ethoxy}-nicotinonitrile

HRID 2191119Notes

Reaction equation

HRID 2191119 reaction equation
ClC1C=CC(OCC2CCNCC2C2C=CC(Cl)=CC=2)=[N:6]C=1.Cl.C([N:31]1[CH2:36][CH2:35][C@H:34]([C@@H:37]([O:39][C:40]2[CH:45]=[CH:44][C:43]([C:46](F)(F)F)=[CH:42][N:41]=2)[CH3:38])[C@@H:33]([C:50]2[CH:55]=[CH:54][C:53]([Cl:56])=[CH:52][CH:51]=2)[CH2:32]1)C1C=CC=CC=1>>[Cl:56][C:53]1[CH:52]=[CH:51][C:50]([C@@H:33]2[C@@H:34]([C@@H:37]([O:39][C:40]3[CH:45]=[CH:44][C:43]([C:46]#[N:6])=[CH:42][N:41]=3)[CH3:38])[CH2:35][CH2:36][NH:31][CH2:32]2)=[CH:55][CH:54]=1

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 594381752-{(S)-1-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethoxy}-5-trifluoromethyl-pyridineHCID 712055575-chloro-2-[(3RS, 4RS)-3-(4-chloro-phenyl)-piperidin-4-ylmethoxy]-pyridine

Product 1

HCID 594381476-{(S)-1-[(3S,4S)-3-(4-Chloro-phenyl)-piperidin-4-yl]-ethoxy}-nicotinonitrile

Procedure

In analogy to the procedure described for the synthesis of 5-chloro-2-[(3RS, 4RS)-3-(4-chloro-phenyl)-piperidin-4-ylmethoxy]-pyridine; hydrochloride (example 1, step h) the title compound was prepared from 2-{(S)-1-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethoxy}-5-trifluoromethyl-pyridine as white foam as the respective HCl salt. MS (m/e): 342.1 [(M+H)+].

Sources & evidence

ORD record
ord-c2d6afed470545a5b6c27ed376d8046e
Source dataset
uspto-grants-2012_12
Patent number
US08324248B2

Reaction notes

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