Phenyl-2-thienylmethyl chloride → 4-(phenyl-2-thienylmethoxy)-1-[4-(2-nitrophenoxy)-2(Z)-butenyl]piperidine

HRID 1612849Notes

Reaction equation

HRID 1612849 reaction equation
[C:1]1([CH:7](Cl)[C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21]/[CH:22]=[CH:23]\[CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N+:32]([O-:34])=[O:33])[CH2:17][CH2:16]1.OC1CCN(C/C=C/COC2C=CC=CC=2[N+]([O-])=O)CC1>>[C:1]1([CH:7]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[O:14][CH:15]2[CH2:16][CH2:17][N:18]([CH2:21]/[CH:22]=[CH:23]\[CH2:24][O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[N+:32]([O-:34])=[O:33])[CH2:19][CH2:20]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 10512583Phenyl-2-thienylmethyl chlorideHCID 197767194-hydroxy-1-[4-(2-nitrophenoxy)-2(E)-butenyl]piperidineHCID 678783434-hydroxy-1-[4-(2-nitrophenoxy)-2(Z)-butenyl]piperidine

Product 1

HCID 678790494-(phenyl-2-thienylmethoxy)-1-[4-(2-nitrophenoxy)-2(Z)-butenyl]piperidine

Procedure

The procedure of Example 39 (a) was repeated except for using phenyl-2-thienylmethyl chloride and 4-hydroxy-1-[4-(2-nitrophenoxy)-2(Z)-butenyl]piperidine instead of phenyl-2-thienylmethyl chloride and 4-hydroxy-1-[4-(2-nitrophenoxy)-2(E)-butenyl]piperidine to give oily 4-(phenyl-2-thienylmethoxy)-1-[4-(2-nitrophenoxy)-2(Z)-butenyl]piperidine.

Sources & evidence

ORD record
ord-c834ac93cae64bdd91555054e46d329c
Source dataset
uspto-grants-1993_03
Patent number
US05190959

Reaction notes

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