Benzyl Bromide → 1-Benzyl-4-(3-phenylpropyl)-1,2,3,6-tetrahydropyridine

HRID 380526Notes

Reaction equation

[C:1]1([CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH4-].[Na+].[OH-].[Na+]>C(O)C>[CH2:16]([N:13]1[CH2:12][CH:11]=[C:10]([CH2:9][CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:15][CH2:14]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1.7 g (8.6 mmol) of 4-(3-phenylpropyl)pyridine and 1.5 mL of benzylbromide in 5 mL of ethanol was stirred at rt for 0.5 h. To the reaction mixture was added 10 mL of ethanol and the mixture was cooled to 0° C. To this mixture was added 0.5 g (13.2 mmol) of NaBH4 small portions over a period of 1 h. To the reaction mixture was then added 5 mL of a 1N NaOH solution and the mixture was partitioned between 200 mL of ether and 50 mL of H2O. The combined organic fractions were washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ethyl acetate, 9:1) to give the title compound.

Workup

customthe mixture was partitioned between 200 mL of ether and 50 mL of H2O
washThe combined organic fractions were washed with sat'd NaCl solution
dry with materialdried over MgSO4
filtrationfiltered
concentrationthe filtrate was concentrated
customThe residue was purified by chromatography (silica, hexanes:ethyl acetate, 9:1)

Sources & evidence

ORD record: ord-b0d115a15d0c4706869f7976196e947d
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06303593B1

Reaction notes

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