N-(3-chloropropyl)piperidine hydrochloride → 4-Naphthyl-1-(3-Piperidylpropyl)piperidine Hydrochloride
Reaction equation
[C:1]1([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.[Cl:18]CCCN1CCCCC1.Cl.ClCCC[N:33]1[CH2:38][CH2:37][CH2:36][CH:35]([C:39]2C=CC(OC)=[CH:41][CH:40]=2)[CH2:34]1>>[ClH:18].[C:1]1([CH:11]2[CH2:16][CH2:15][N:14]([CH2:41][CH2:40][CH2:39][CH:35]3[CH2:36][CH2:37][CH2:38][NH:33][CH2:34]3)[CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1Participants
Procedure
Using 4-(1-naphthyl)piperidine (149 mg, 0.60 mmol) and 1-(3-chloropropyl)piperidine hydrochloride (166 mg, 0.84 mmol) instead of 4-(3-indolyl)piperidine and 1-(3-chloropropyl)-3-(4-methoxyphenyl)piperidine hydrochloride respectively, reaction, extraction, and concentration were carried out in the same procedure as Example 2. The resulting crude product was purified by column chromatography on a silica gel (silica gel NH-DM 1020 produced by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate=2:1) to afford a free form (202 mg) of the title compound as a yellow viscous oil. After adding hydrochloric acid/methanol to a solution of the free form in methanol, the mixture was concentrated and was then recrystallized from methanol/ether to afford the title compound (85 mg, yield: 35%) as white crystals.
Workup
- customreaction, extraction, and concentration
- customThe resulting crude product was purified by column chromatography on a silica gel (silica gel NH-DM 1020 produced by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate=2:1)
Sources & evidence
- ORD record
- ord-bdf6453207174bb1a5c1cfad30f2536d
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06642228B1
Reaction notes
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