3-(Dimethylamino)propyl chloride hydrochloride → 2-(3-(4-Naphthylpiperidyl)propyl)isoindoline 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][CH2:19][CH2:20][CH2:21][N:22]1[CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23]1.Cl.CN(C)CCCCl>>[ClH:18].[C:1]1([CH:11]2[CH2:16][CH2:15][N:14]([CH2:19][CH2:20][CH2:21][N:22]3[CH2:23][C:24]4[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:30]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 (124 mg, 0.50 mmol) and 2-(3-chloropropyl)isoindoline hydrochloride (139 mg, 0.72 mmol) instead of 4-(3-indolyl)piperidine and 3-dimethylaminopropyl chloride hydrochloride respectively, reaction, extraction, and concentration were carried out in the same procedure as Example 4. 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; chloroform:methanol=20:1) to afford a free form (158 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 (91 mg, yield: 44%) 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; chloroform:methanol=20:1)
Sources & evidence
- ORD record
- ord-e62ada549e7c42ba8d62fde20436d8fe
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06642228B1
Reaction notes
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