N-(3-chloropropyl)piperidine hydrochloride → 3-(1-(3-Piperidylpropyl)-4-piperidyl)-2-aza-1-oxaindene Hydrochloride
Reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:2]1.Cl.[Cl:17]CCCN1CCCCC1.Cl.ClCCC[N:32]1[CH2:37][CH2:36][CH2:35][CH:34]([C:38]2C=CC(OC)=[CH:40][CH:39]=2)[CH2:33]1>>[ClH:17].[NH:32]1[CH2:37][CH2:36][CH2:35][CH:34]([CH2:38][CH2:39][CH2:40][N:13]2[CH2:14][CH2:15][CH:10]([C:3]3[C:4]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[O:1][N:2]=3)[CH2:11][CH2:12]2)[CH2:33]1Participants
Procedure
Using 4-(3-benzisoxazolyl)piperidine (191 mg, 0.80 mmol) and 1-(3-chloropropyl)piperidine hydrochloride (222 mg, 1.1 mmol) instead of 4-(3-indolyl)piperidine and 1-(3-chloropropyl)-3-(4-methoxyphenyl)piperidine hydrochloride respectively, reaction 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=3:1) to afford a free form (236 mg) of the title compound as a pale 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 (277 mg, yield: 86%) as white crystals.
Workup
- customreaction 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=3:1)
Sources & evidence
- ORD record
- ord-bc7761848a8249f6bbadf49b498c6e21
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06642228B1
Reaction notes
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