N-(3-chloropropyl)piperidine hydrochloride → HCID 70038547, compound

HRID 478208Notes

Reaction equation

HRID 478208 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]CCC[N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.Cl.CN(C)[CH2:31][CH2:32][CH2:33]Cl>>[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]([CH2:31][CH2:32][CH2:33][CH:26]2[CH2:25][CH2:24][CH2:23][NH:22][CH2:27]2)[CH2:13][CH2:12]1

Participants

4

Reactant 3

HCID 79624N-(3-chloropropyl)piperidine hydrochlorideHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 220292644-(Naphthalen-2-yl)piperidine

Product 1

HCID 70038547HCID 70038547, compound

Procedure

Using 4-(2-naphthyl)piperidine (167 mg, 0.67 mmol) and 1-(3-chloropropyl)piperidine hydrochloride (198 mg, 1.0 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; hexane:chloroform=1:1) to afford a free form (187 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 ethanol to afford the title compound (177 mg, yield: 64%) as white crystals.

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; hexane:chloroform=1:1)

Sources & evidence

ORD record
ord-3e606ca8fdd04054a58d9fdfb48437b0
Source dataset
uspto-grants-2003_11
Patent number
US06642228B1

Reaction notes

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