N-(3-chloropropyl)piperidine hydrochloride → 3-(1-(3-Piperidylpropyl)-3-piperidyl)indole Hydrochloride

HRID 478212Notes

Reaction equation

HRID 478212 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][CH2:13][NH:12][CH2:11]2)=[CH:2]1.Cl.[Cl:17]CCC[N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.Cl.CN(C)[CH2:30][CH2:31][CH2:32]Cl>>[ClH:17].[NH:21]1[CH2:22][CH2:23][CH2:24][CH:25]([CH2:30][CH2:31][CH2:32][N:12]2[CH2:13][CH2:14][CH2:15][CH:10]([C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][CH:2]=3)[CH2:11]2)[CH2:26]1

Participants

4

Reactant 3

HCID 79624N-(3-chloropropyl)piperidine hydrochlorideHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 153894433-(Piperidin-3-YL)-1H-indole

Product 1

HCID 700380983-(1-(3-Piperidylpropyl)-3-piperidyl)indole Hydrochloride

Procedure

Using 3-(3-indolyl)piperidine (104 mg, 0.44 mmol) and 1-(3-chloropropyl)piperidine hydrochloride (122 mg, 0.62 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 (125 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 freeze-dried to afford the title compound (129 mg, yield: 74%) as a white amorphous solid.

Workup

  1. customreaction, extraction, and concentration
  2. 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-f867ca80f3bf4a9a8ba5a5def33fd023
Source dataset
uspto-grants-2003_11
Patent number
US06642228B1

Reaction notes

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