(3-Bromopropyl)benzene → HCID 54429308, compound

HRID 722683Notes

Reaction equation

HRID 722683 reaction equation
[N:1]1([CH2:7][C:8]2[CH:15]=[CH:14][C:11]([CH2:12][O-:13])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Na+].[C:17]1([CH2:23][CH2:24][CH2:25]Br)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[C:17]1([CH2:23][CH2:24][CH2:25][O:13][CH2:12][C:11]2[CH:10]=[CH:9][C:8]([CH2:7][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[CH:15][CH:14]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 12503(3-Bromopropyl)benzeneHCID 86608799HCID 86608799, compound

Product 1

HCID 54429308HCID 54429308, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-(Piperidinomethyl)benzoic acid methyl ester (22 mmol) in dry tetrahydrofurane was added dropwise to a suspension of 44 mmol of lithium aluminium hydride in 30 ml of dry tetrahydrofurane at 0° C. After refluxing for 2 hours a saturated solution of ammonium chloride in water was added dropwise. After stirring for 12 hours at ambient temperature the organic layer was isolated and the aqueous layer extracted with methylene chloride. The organic extracts were combined and the solvent was evaporated under reduced pressure. The residue was crystallized with maleic acid from diethyl ether/2-propanol (Yield: 91%). Sodium 4-(piperidinomethyl)benzyl alcoholate (5 mmol) and 6 mmol of 3-phenylpropyl bromide in 10 ml of dry toluene were refluxed for 6 hours. The solvent was evaporated under reduced pressure. The residue was purified by rotatory chromatography on silica gel using methylene chloride/ammonia atmosphere as eluent. The product was crystallized with oxalic acid from diethyl ether/ethanol.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customThe residue was purified by rotatory chromatography on silica gel
  3. customThe product was crystallized with oxalic acid from diethyl ether/ethanol

Sources & evidence

ORD record
ord-d24b1f57e81f47d79478350280ecb3eb
Source dataset
uspto-grants-2006_11
Patent number
US07138413B1

Reaction notes

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