Epichlorohydrin → 1-(3-Methyl-4-benzyloxynaphthoxy)-3-[4-(2-fluorophenyl)-1-piperazinyl] propan-2-ol hydrochloride

HRID 277633Notes

Reaction equation

HRID 277633 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([OH:19])=[CH:11][C:10]=1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:27][CH2:28][CH:29]1[CH2:31][O:30]1.Cl.[F:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1.C(N(CC)CC)C>>[ClH:27].[CH3:20][C:10]1[CH:11]=[C:12]([O:19][CH2:28][CH:29]([OH:30])[CH2:31][N:43]2[CH2:42][CH2:41][N:40]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[F:33])[CH2:45][CH2:44]2)[C:13]2[C:18]([C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2

Participants

6

Reactant 5

HCID 7835EpichlorohydrinHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 27346981-(2-Fluorophenyl)piperazine HydrochlorideHCID 120516524-Benzyloxy-3-methylnaphthol

Product 1

HCID 226254131-(3-Methyl-4-benzyloxynaphthoxy)-3-[4-(2-fluorophenyl)-1-piperazinyl] propan-2-ol hydrochlorideYield 57.7%

Procedure

Using 5.3 g (0.02 mol) of 4-benzyloxy-3-methylnaphthol, 2.8 g (0.02 mol) of anhydrous potassium carbonate, 9.3 g (0.10 mol) of chloromethyloxirane, 4.3 g (0.02 mol) of 1-(2-fluorophenyl)piperazine hydrochloride and 2.0 g (0.02 mol) of triethylamine, reaction was carried out as in Example 1-A to give 6.2 g of white crystals, m.p. 218-220° C. (decomp.).

Sources & evidence

ORD record
ord-8eb5b2a72c584945bc786e773d3e341d
Source dataset
uspto-grants-2002_03
Patent number
US06358515B2

Reaction notes

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