3-(Dimethylamino)propyl chloride hydrochloride → 2-(3-(4-(2-Naphthyl)piperidyl)propyl)isoindoline Hydrochloride
Reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]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].[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]1[CH2:16][CH2:15][N:14]([CH2:19][CH2:20][CH2:21][N:22]2[CH2:23][C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:30]2)[CH2:13][CH2:12]1Participants
Procedure
Using 4-(2-naphthyl)piperidine (149 mg, 0.60 mmol) and 2-(3-chloropropyl)isoindoline hydrochloride (209 mg, 0.90 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) to afford a free form (119 mg) of the title compound as a colorless 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 ethanol/ethyl acetate to afford the title compound (110 mg, yield: 41%) 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)
Sources & evidence
- ORD record
- ord-68b4a59fd5624c419ede2c74cfe0994c
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06642228B1
Reaction notes
Loading…