2-(hexamethyleneimino)ethyl chloride HCl → 1-(2-{4-[2-(3-Fluoro-phenyl)-6-methoxy-naphthalen-1-yloxy]phenoxy}-ethyl)-azepane hydrochloride

HRID 1513875Notes

Reaction equation

HRID 1513875 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=3)[C:9]=2[O:20][C:21]2[CH:35]=[CH:34][C:24]([O:25][CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:23][CH:22]=2)[CH:5]=[CH:6][CH:7]=1.Cl.N(=CCCl)[CH2:38]CCCCC[Cl:44]>>[ClH:44].[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=3)[C:9]=2[O:20][C:21]2[CH:22]=[CH:23][C:24]([O:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][CH2:38][CH2:31][CH2:32][CH2:33]3)=[CH:34][CH:35]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 534452772-(hexamethyleneimino)ethyl chloride HClHCID 575525301-(2-{4-[2-(3-Fluoro-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenoxy}-ethyl)-piperidine

Product 1

HCID 670045941-(2-{4-[2-(3-Fluoro-phenyl)-6-methoxy-naphthalen-1-yloxy]phenoxy}-ethyl)-azepane hydrochloride

Procedure

Prepare this compound following the procedure to make 1-(2-{4-[2-(3-fluoro-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenoxy}-ethyl)-piperidine above, using 2-(hexamethyleneimino)-ethyl chloride hydrochloride to get a 100% yield of the free base of the title compound after radial chromatography. Form the hydrochloride salt by adding 0.8 mL of a 1 M HCl in Et2O solution: mass spectrum (ion spray) m/z=4.86 (M−Cl).

Workup

  1. customPrepare this compound

Sources & evidence

ORD record
ord-dbe7665fcc8b4510944a19bd67dd6413
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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