(3-Bromopropyl)benzene → 1-(3-(3-Phenylpropoxy)propyl)piperidine

HRID 604382Notes

Reaction equation

HRID 604382 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][O-:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Na+].[C:12]1([CH2:18][CH2:19][CH2:20]Br)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1OCCOCCOCCOCCOC1>C1(C)C=CC=CC=1>[N:1]1([CH2:7][CH2:8][CH2:9][O:10][CH2:20][CH2:19][CH2:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 12503(3-Bromopropyl)benzeneHCID 3633615-Crown-5HCID 23694275Sodium 3-piperidinopropanolate

Product 1

HCID 99033431-(3-(3-Phenylpropoxy)propyl)piperidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Sodium 3-piperidinopropanolate (20 mmol), 20 mmol of 3-phenylpropyl bromide, and 0.5 mmol of 15-crown-5 in 30 ml of dry toluene were refluxed for 4 hours. The solvent was evaporated and the residue purified by column chromatography on silica gel (eluent: methylene chloride/methanol/aqueous ammonia (90/10/0.5)). After removing the solvent under reduced pressure the residue was crystallized with oxalic acid from diethyl ether/ethanol.

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by column chromatography on silica gel (eluent: methylene chloride/methanol/aqueous ammonia (90/10/0.5))
  3. customAfter removing the solvent under reduced pressure the residue
  4. customwas crystallized with oxalic acid from diethyl ether/ethanol

Sources & evidence

ORD record
ord-82451b3f9a114011b4d0c2fe15cea173
Source dataset
uspto-grants-2011_03
Patent number
US07910605B2

Reaction notes

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