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

HRID 277635Notes

Reaction equation

HRID 277635 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:28][CH2:29][CH:30]1[CH2:32][O:31]1.[ClH:33].Cl.[CH3:35][O:36][C:37]1[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=[CH:39][C:38]=1[N:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1.C(N(CC)CC)C>>[ClH:28].[ClH:33].[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:38]2[CH:39]=[CH:40][C:41]([O:43][CH3:44])=[CH:42][C:37]=2[O:36][CH3:35])[CH2:50][CH2:49]1

Participants

6

Reactant 5

HCID 7835EpichlorohydrinHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 22625378HCID 22625378, compoundHCID 226254094-Benzoyloxy-2-methylnaphthol

Product 1

HCID 226253921-(2-Methyl-4-hydroxynaphthoxy)-3-[4-(2,4-dimethoxyphenyl)-1-piperazinyl] propan-2-ol dihydrochlorideYield 13.3%

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-(2,4-dimethoxyphenyl)piperazine dihydrochloride and 2.0 g (0.02 mol) of triethylamine, reaction was carried out as in Examples 2 and 4 to give 0.7 g of crystals, m.p. 175-177° C. (decomp.).

Sources & evidence

ORD record
ord-3d0e2e1168804c138e4e559302229c25
Source dataset
uspto-grants-2002_03
Patent number
US06358515B2

Reaction notes

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