1-(3,4-Dihydro-2-naphthyl)pyrrolidine → 1-[1-(3-Benzyloxy-4-nitrobenzyl)-3,4-dihydro-1H-naphthalen-2-ylidene]-pyrrolidinium Bromide

HRID 660564Notes

Reaction equation

HRID 660564 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]=1[N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.[CH2:16]([O:23][C:24]1[CH:29]=[C:28]([CH2:30][Br:31])[CH:27]=[CH:26][C:25]=1[N+:32]([O-:34])=[O:33])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC#N>[Br-:31].[CH2:16]([O:23][C:24]1[CH:29]=[C:28]([CH:27]=[CH:26][C:25]=1[N+:32]([O-:34])=[O:33])[CH2:30][CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]1=[N+:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 888891-(3,4-Dihydro-2-naphthyl)pyrrolidineHCID 621150422-Benzyloxy-4-bromomethyl-1-nitrobenzene

Product 1

HCID 688390331-[1-(3-Benzyloxy-4-nitrobenzyl)-3,4-dihydro-1H-naphthalen-2-ylidene]-pyrrolidinium Bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-(3,4-dihydronaphthalen-2-yl)-pyrrolidine (Syn. Comm. 33, 2215 (2003)) (450 mg, 2.26 mmol) and 2-benzyloxy-4-bromomethyl-1-nitrobenzene (Example 83, step C) (730 mg, 2.26 mmol) in 20 mL CH3CN is stirred at RT for 1 h. The solvent is removed under reduced pressure to give the title compound as a red solid.

Workup

  1. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-758fed7dc0a445afa06c0341aa628cee
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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