Epichlorohydrin → 1-(2-Methyl-4-hydroxynaphthoxy)-3-[4-(3,4-dimethoxyphenyl)-1-piperazinyl]propan-2-ol

HRID 277634Notes

Reaction equation

C([O:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](O)=[C:12]([CH3:21])[CH:11]=1)(=O)C1C=CC=CC=1.C(=O)([O-])[O-:23].[K+].[K+].Cl[CH2:29][CH:30]1[CH2:32][O:31]1.Cl.Cl.[CH3:35][O:36][C:37]1[CH:38]=[C:39]([N:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)[CH:40]=[CH:41][C:42]=1[O:43][CH3:44].C(N(CC)CC)C>>[CH3:21][C:12]1[CH:11]=[C:10]([OH:9])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[O:31][CH2:32][CH:30]([OH:23])[CH2:29][N:48]1[CH2:47][CH2:46][N:45]([C:39]2[CH:40]=[CH:41][C:42]([O:43][CH3:44])=[C:37]([O:36][CH3:35])[CH:38]=2)[CH2:50][CH2:49]1

Participants

Reactant 5

HCID 7835Epichlorohydrin

HCID 8471Triethylamine

HCID 11430Potassium Carbonate

HCID 226254071-(3,4-Dimethoxyphenyl)piperazine dihydrochloride

HCID 226254094-Benzoyloxy-2-methylnaphthol

Product 1

HCID 226253851-(2-Methyl-4-hydroxynaphthoxy)-3-[4-(3,4-dimethoxyphenyl)-1-piperazinyl]propan-2-olYield 8.8%

Procedure

Using 2.8 g (0.01 mol) of 4-benzoyloxy-2-methylnaphthol, 1.4 g (0.01 mol) of anhydrous potassium carbonate, 4.6 g (0.05 mol) of chloromethyloxirane, 2.9 g (0.01 mol) of 1-(3,4-dimethoxyphenyl)piperazine dihydrochloride and 2.0 g (0.02 mol) of triethylamine, reaction was carried out as in Examples 3 and 4 to give 0.4 g of white crystals, m.p. 180-182° C. (decomp.).

Sources & evidence

ORD record: ord-ba651ba37ecd4920b08c5bcff6415d40
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06358515B2

Reaction notes

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